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In Portugal's first knockout match, Ronaldo's only attempt on goal was parried by Croatia's goalkeeper Danijel Subašić into the path of Ricardo Quaresma, whose finish then secured a 1–0 win late in extra time. After his team progressed past Poland on penalties, with Ronaldo scoring Portugal's opening penalty, he became the first player to participate in three European Championship semi-finals; he scored the opener in a 2–0 win against Wales, equalling Michel Platini as the competition's all-time top scorer with nine goals. In the final against hosts France, Ronaldo was forced off after just 25 minutes following a challenge from Dimitri Payet, despite multiple treatments and attempts to play on, he was stretchered off the pitch and replaced by Quaresma. During extra time, substitute Eder scored in the 109th minute to earn Portugal a 1–0 victory. As team captain, Ronaldo lifted the trophy in celebration of his country's first triumph in a major tournament. He was awarded the Silver Boot as the joint second-highest goalscorer, with three goals and three assists, and was named to the team of the tournament for the third time in his career.

Following the Euro 2016 success, Ronaldo played his first professional match on his home island of Madeira on 28 March 2017 at age 32, opening a 2–3 friendly defeat to Sweden at the Estádio dos Barreiros. With the goal, he tied with Miroslav Klose on 71 goals as the third-highest scoring European in international football.

In Portugal's opening match of the 2017 FIFA Confederations Cup against Mexico on 17 June, Ronaldo set up Quaresma's opening goal in a 2–2 draw. Three days later, he scored in a 1–0 win over hosts Russia. On 24 June, he scored from a penalty in a 4–0 win over New Zealand, which saw Portugal top their group and advance to the semi-finals of the competition; with his 75th international goal, Ronaldo also equalled Sándor Kocsis as the second-highest European international goalscorer of all-time, behind only Ferenc Puskás. He was named man of the match in all three of Portugal's group stage matches. Ronaldo left the competition early; after Chile defeated Portugal 3–0 on penalties in the semi-finals, he was allowed to return home to be with his newborn children, and missed Portugal's third-place play-off match in which Portugal defeated Mexico 2–1 after extra time.

On 31 August 2017, Ronaldo scored a hat-trick in a 5–1 win in a 2018 World Cup qualifying match over the Faroe Islands, which saw him overtake Pelé and equal Hussein Saeed as the joint-fifth-highest goalscorer in international football with 78 goals. These goals brought his tally in the World Cup qualifiers to 14, equalling Predrag Mijatović's record for most goals in a single UEFA qualifying campaign, and also saw him break the record for the most goals scored in a European qualifying group, overtaking the previous record of 13 goals set by David Healy and Robert Lewandowski. Ronaldo's hat-trick took his World Cup qualifying goals total to 29, making him the highest scorer in UEFA qualifiers, ahead of Andriy Shevchenko, and the highest goalscorer in World Cup qualifying and finals matches combined with 32 goals, ahead of Miroslav Klose. Ronaldo later added to this tally by scoring a goal against Andorra in a 2–0 win.

On 15 June 2018, Ronaldo became the oldest player to score a hat-trick in a FIFA World Cup match, helping Portugal secure a 3–3 draw against Spain (his third goal a 30-yard curling free kick with two minutes remaining) in their opening match. In doing so, he became the first Portuguese player to score a goal in four World Cups and one of four players of any nationality to do so. On 20 June, Ronaldo scored the only goal in a 1–0 win against Morocco, breaking Puskás' record as the highest European goalscorer of all-time, with 85 international goals. In the final group match against Iran on 25 June, Ronaldo missed a penalty in an eventual 1–1 draw which saw Portugal progress to the second round as group runners-up behind Spain. On 30 June, Portugal were eliminated following a 2–1 defeat to Uruguay in the last 16. For his performances in the tournament, Ronaldo was named in the World Cup Dream Team.

After the World Cup, Ronaldo missed six international matches, including the entire league phase of the 2018–19 UEFA Nations League, but played for hosts Portugal in the inaugural Nations League Finals in June 2019. In the semi-finals on 5 June, he scored a hat-trick against Switzerland to reach the final. Upon scoring the opening goal, he became the first player to score in 10 consecutive international competitions, breaking the record he previously shared with Ghana's Asamoah Gyan. In the final of the tournament four days later, Portugal defeated the Netherlands 1–0.

On 10 September 2019, Ronaldo scored four goals in a 5–1 away win over Lithuania in a Euro 2020 qualifying match; in the process, he overtook Robbie Keane (23 goals) as the player with most goals in the UEFA European Championship qualifying, setting a new record with 25 goals. He also set a new record for scoring against the most national teams, 40, while also completing his eighth international hat-trick. On 14 October, he scored his 700th senior career goal for club and country from the penalty spot, in his 974th senior career appearance, a 2–1 away loss to Ukraine in a Euro 2020 qualifier. On 17 November, Ronaldo scored his 99th international goal in a 2–0 win over Luxembourg, leading Portugal to qualify for Euro 2020. On 8 September 2020, Ronaldo scored his 100th and 101st international goals in a 2–0 away win over Sweden in a 2020–21 UEFA Nations League match, becoming only the second male player ever to achieve this milestone (after Ali Daei of Iran) and the first in Europe. On 13 October, the FPF announced that Ronaldo tested positive for COVID-19 while being asymptomatic. By 30 October, Ronaldo had recovered.

On 15 June 2021, Ronaldo scored twice in Portugal's first game of Euro 2020, a 3–0 win against Hungary in Budapest. This took him to a total of 11 European Championship goals, two clear of Michel Platini, as the all-time top goalscorer in the competition's history. He also became the first player to score at five Euros, and in eleven consecutive tournaments. The brace made Ronaldo the oldest player to score two goals in a match in the competition, and the oldest player to score for Portugal at a major tournament. On 23 June, he scored two penalties in Portugal's 2–2 draw with France in their final group stage match, equalling Daei's record of 109 international goals. On 27 June, Portugal were eliminated following a 1–0 loss against Belgium in the round of 16. Ronaldo finished the tournament with five goals (tied with Czech Patrik Schick) and one assist, earning him the Golden Boot.

On 1 September, Ronaldo scored two headed goals, with his second coming seconds before the full-time whistle, in a 2–1 home win against the Republic of Ireland in a World Cup qualifier at the Estádio Algarve, which saw him pass Ali Daei to become the sole record holder by breaking the men's international scoring record with his 110th and 111th international goals. On 9 October, he scored the opening goal in a 3–0 friendly win over Qatar at the Estádio Algarve; with his 181st international appearance, he also overtook Sergio Ramos's record for the most international caps received by a European player. In the following match against Luxembourg on 12 October, also played at the Estádio Algarve, Ronaldo scored a hat-trick in a 5–0 win for Portugal, and became the first player to score 10 hat-tricks in men's international football.

Ronaldo was named in Portugal's squad for the 2022 FIFA World Cup in Qatar, making it his fifth World Cup. On 24 November, in Portugal's opening match against Ghana, Ronaldo scored a penalty kick and became the first male player to score in five different World Cups. In the last group game against South Korea, Ronaldo received criticism from his own coach for his reaction at being substituted. He was dropped from the starting line-up for Portugal's last 16 match against Switzerland, marking the first time since Euro 2008 that he had not started a game for Portugal in a major international tournament, and the first time Portugal had started a knockout game without Ronaldo in the starting line-up at an international tournament since Euro 2000. He came off the bench late on as Portugal won 6–1, their highest tally in a World Cup knockout game since the 1966 World Cup, with Ronaldo's replacement Gonçalo Ramos scoring a hat-trick. Portugal employed the same strategy in the quarter-finals against Morocco, with Ronaldo once again coming off the bench; in the process, he equalled Bader Al-Mutawa's international appearance record, becoming the joint–most capped male footballer of all time, with 196 caps. Portugal lost 1–0, however, with Morocco becoming the first CAF nation ever to reach the World Cup semi-finals.

A versatile attacker, Ronaldo is capable of playing on either wing as well as through the centre of the pitch, and, while ostensibly right-footed, is very strong with both feet. Tactically, Ronaldo has undergone several evolutions throughout his career. While at Sporting and during his first season at Manchester United, he was typically deployed as a traditional winger on the right side of midfield, where he regularly looked to deliver crosses into the penalty area. In this position, he was able to use his pace and acceleration, agility and technical skills to take on opponents in one-on-one situations. Ronaldo became noted for his dribbling and flair, often displaying an array of tricks and feints, such as the step overs and so-called 'chops' that became his trademark; he has also been known to use the flip-flap.

As Ronaldo matured, he underwent a major physical transformation, developing a muscular body type that allowed him to retain possession of the ball under pressure, and strong legs that enabled an outstanding jumping ability. His strength and jumping ability, combined with his elevation, heading accuracy and height of , give him an edge in winning aerial duels. These attributes allow him to function as a target-man and make him an aerial goal threat in the penalty area; consequently, many of his goals have been headers. Allied with his increased stamina and work-rate, his goalscoring ability improved drastically on the left wing where he was given the positional freedom to move into the centre to finish attacks. He has also increasingly played a creative role for his team, often dropping deep to pick up the ball, participate in the build-up of plays and create chances for his teammates, courtesy of his vision and passing ability.

In his final seasons at United, Ronaldo played an even more attacking and central role, functioning both as a striker and as a supporting forward, or even as an attacking midfielder on occasion. He developed into a prolific goalscorer, capable of finishing well both inside the penalty area and from distance with an accurate and powerful shot, courtesy of his striking ability. An accurate penalty kick taker, he also became a set piece specialist, renowned for his powerful, bending free kicks. When taking free kicks, Ronaldo is known for using the "knuckleball" technique, which was developed by Juninho Pernambucano. He also adopts a trademark stance before striking the ball, which involves him standing with his legs far apart. Regarding Ronaldo's unique style of taking free kicks, former Manchester United assistant manager Mike Phelan commented: "People used to put the ball down, walk away, run up and hit it. He brought in a more dynamic showmanship. He places the ball down, the concentration level is high, he takes his certain amount of steps back so that his standing foot is in the perfect place to hit the ball in the sweet spot. He is the ultimate showman. He has that slight arrogance. When he pulls those shorts up and shows his thighs, he is saying 'All eyes on me' and this is going in. He understands the marketing side of it. The way he struts up and places it; the world is watching him."

At Real Madrid, Ronaldo continued to play a more offensive role, while his creative and defensive duties became more limited, although not entirely diminished. Initially deployed as a centre forward by managers Manuel Pellegrini and José Mourinho, he was later moved back onto the left wing, though in a free tactical role; this position allowed him to drift into the centre at will to get onto the end of crosses and score, or draw out defenders with his movement off the ball and leave space for teammates to exploit. Madrid's counter-attacking style of play also allowed him to become a more efficient and consistent player, as evidenced by his record-breaking goalscoring feats. While he mainly drew praise in the media for his prolific goalscoring, Ronaldo also demonstrated his ability as an effective creator in this role. This unique role has been described by pundits as that of a "false", "attacking", or "goalscoring winger", as Ronaldo effectively almost functioned as a striker at times with his central runs into the penalty area, despite actually playing on the left flank. From 2013 onwards, under manager Carlo Ancelotti, he effectively adapted his style to the physical effects of ageing with increasingly reduced off-the-ball movement and general involvement, completing fewer dribbles and passes per game, and instead focusing on short-distance creating and goalscoring. Since 2017, Ronaldo adapted his style of play yet again to become more of a free-roaming centre forward under manager Zinedine Zidane, a role in which he continued to excel and maintain a prolific goalscoring record; in this position, he earned praise in the media for his intelligent movement both on and off the ball, positional sense, link-up play and finishing, as well as his ability to lose or anticipate his markers, find space in the box and score from few touches or opportunities.

In his first season at Juventus, Ronaldo continued to play in a variety of different attacking roles under manager Massimiliano Allegri, depending on whom he was partnered with. While he had occupied an increasingly offensive role in his final years at Real Madrid, at times he functioned in a free role at Juventus, either as a lone striker or in his trademark role on the left wing, in a 4–2–3–1 or 4–3–3 formation, in which he often switched positions with Mario Mandžukić. In this role, he was also given licence to drop deep or even out wide onto the right flank to receive the ball, and be more involved in the build-up of plays; as such, aside from scoring goals himself, he began to take on opponents and create chances for other players with greater frequency than he had in his final seasons with Real Madrid. Off the ball, he was also capable of creating space for teammates with his movement and attacking runs into the box, or finishing off chances with his head or feet by getting onto the end of his teammates' crosses. On occasion he also played in an attacking partnership alongside Mandžukić in a 4–3–1–2, 4–4–2, or 3–5–2 formation. He continued to play a similar role in his second season with the club under manager Maurizio Sarri.

Ronaldo is widely regarded as one of the two best players of his generation, alongside Lionel Messi. Winning his first Ballon d'Or in 2008 by a record-high vote count at age 23, over the next decade Ronaldo has often featured in debates concerning who is the greatest player in history. Acclaimed for his prolific and consistent goal-scoring, he is considered a decisive player who is also a game changer, especially in important and high-pressured situations.

Ronaldo is noted for his work ethic, elite body conditioning and dedication to improvement on the training pitch, as well being regarded as a natural leader. On his longevity and "extraordinary commitment to physical preparation", Adam Bate of Sky Sports said: "Dedication is a huge part of staying at the top and Ronaldo's focus is perhaps unparalleled within the game." While stating they were stylistically different players who shared an equal desire to score goals, former Brazil international Ronaldo praised Cristiano's approach to training, arguing that "there are so few players who take care of their body like he does. I trained because I had to, he does it because he loves it." His drive and determination to succeed are fuelled by a desire to be talked about alongside other greats such as Pelé and Diego Maradona once retiring. He is credited, along with his compatriot, coach José Mourinho, with inspiring changing fortunes of Portuguese football in and . At times, he has been criticised for simulating when tackled. He was also occasionally criticised early in his career by manager Alex Ferguson, teammates and the media for being a selfish or overly flamboyant player. Jonathan Wilson of "The Guardian" opined that Ronaldo had made Juventus, who he joined aged 33 in 2018, weaker, due to "his relative immobility" in his mid-30s, even if his personal goal-scoring output remained high.

During his career, Ronaldo has also been described as having an "arrogant image" on the pitch, with Ronaldo stating that he had become a "victim" because of how he was portrayed in the media. He is often seen moaning, gesticulating and scowling while trying to inspire his team to victory, with Ronaldo insisting that his competitive nature should not be mistaken for arrogance. His managers, teammates and various journalists have said that this reputation has caused an unfair image of him.

Ronaldo has adopted several goal celebrations throughout his career, including one particular celebration which gained widespread coverage in the media, when he squatted and stared directly into a camera on the sidelines of the pitch with his hand on his chin. After scoring a goal, he usually celebrates with a "storming jump" and "turn", before "landing in spread-eagled fashion" into his "signature power stance", while usually simultaneously exclaiming "Sí" (Spanish and Italian for "yes"). This trademark celebration has been dubbed the "Sii" in the media.

Both players have scored in multiple UEFA Champions League finals and have regularly broken the 50-goal barrier in a single season. Sports journalists and pundits regularly weigh the individual merits of both players in an attempt to argue who they believe is the best player in modern football or in the history of the game. It has been compared to several sports rivalries, among them the Muhammad Ali–Joe Frazier rivalry in boxing, the Borg–McEnroe rivalry in tennis and the Senna–Prost rivalry from Formula One motor racing. Some commentators choose to analyse the differing physiques and playing styles of the two, Part of the debate revolves around the contrasting personalities of the two players, as Ronaldo is sometimes depicted as an arrogant and theatrical showoff, while Messi is portrayed as a shy, humble character.

In a 2012 interview, Ronaldo commented on the rivalry, saying: "I think we push each other sometimes in the competition, this is why the competition is so high." Alex Ferguson, Ronaldo's manager during his time at Manchester United, opined: "I don't think the rivalry against each other bothers them. I think they have their own personal pride in terms of wanting to be the best." Messi himself denied any rivalry, saying that it was "only the media, the press, who wants us to be at loggerheads but I've never fought with Cristiano." Responding to the claims that he and Messi do not get on well on a personal level, Ronaldo commented: "We don't have a relationship outside the world of football, just as we don't with a lot of other players." Ronaldo added that in years to come he hopes they can laugh about it together, stating: "We have to look on this rivalry with a positive spirit, because it's a good thing." Representing archrivals Barcelona and Real Madrid, the two players faced each other at least twice every season in the world's biggest club game, "El Clásico", which is among the world's most viewed annual sporting events.

In a debate at Oxford Union in October 2013, when asked whether FIFA president Sepp Blatter preferred Messi or Ronaldo, Blatter paid tribute to the work ethic of the Argentine before taking a swipe at Ronaldo, claiming "one of them has more expenses for the hairdresser than the other." Real Madrid demanded and promptly received a full apology. In response to Blatter's "commander" on the pitch comment, Ronaldo issued his own riposte with a mock-salute celebration after scoring a penalty against Sevilla. In August 2019, Ronaldo and Messi were interviewed while sat next to each other prior to the announcement of the UEFA Men's Player of the Year, with Ronaldo stating: "I pushed him and he pushed me as well. So it's good to be part of the history of football."

As his reputation grew from his time at Manchester United, Ronaldo has signed many sponsorship deals for consumer products, including sportswear, football boots; since November 2012, Ronaldo has worn the Nike Mercurial Vapor personalized CR7 edition, soft drinks, clothing, automotive lubricants, financial services, electronics, and video games. Ronaldo was featured as the cover star of EA Sports' "FIFA" video game "FIFA 18" and was heavily involved in the game's promotion. His "Sii" goal celebration features in the "FIFA" series, accompanied with his own voiceover. He was also the face of "Pro Evolution Soccer", appearing on the covers of the 2008, 2012 and 2013 editions of the game.

With earnings of €720 million (£615 million) from 2010 to 2019, Ronaldo was ranked second in "Forbes" list of The Highest-Paid Athletes Of The Decade, with only boxer Floyd Mayweather Jr. earning more. "Forbes" twice ranked Ronaldo first on its list of the world's highest-paid football players; his combined income from salaries, bonuses and endorsements was $73 million in 2013–14 and $79 million in 2014–15. The latter earnings saw him listed behind only Mayweather on the magazine's list of The World's Highest-Paid Athletes. In 2016, he became the first footballer to top the "Forbes" list of highest-earning athletes, with a total income of $88 million from his salary and endorsements in 2015–16. He topped the list for the second straight year with earnings of $93 million in 2016–17. He is the first footballer and only the third sportsman to earn $1 billion in their career. Ronaldo is one of the world's most marketable sportsmen: "SportsPro" rated him the fifth most marketable athlete in 2012 and eighth most marketable athlete in 2013, with Brazilian footballer Neymar topping both lists. Sports market research company Repucom named Ronaldo the most marketable and most recognised football player in the world in May 2014. He was additionally named in the 2014 Time 100, "Time"s annual list of the most influential people in the world. ESPN named Ronaldo the world's most famous athlete in 2016, 2017, 2018 and 2019.

Ronaldo has established a strong online presence. The most popular sportsperson on social media, he counted over 500 million total followers across Facebook, Twitter and Instagram by February 2021, making him the first person to pass half a billion followers. The most-followed person on Facebook (148 million), the most-followed on Instagram (310 million) and the most-followed sportsperson on Twitter (92 million), his sponsors earned $936 million in media value across his accounts between June 2016 to June 2017. Ronaldo has released two mobile apps. In December 2011, he launched an iPhone game called "Heads Up with Cristiano", created by developer RockLive, and in December 2013, he launched "Viva Ronaldo", a dedicated social networking website and app. Computer security company McAfee produced a 2012 report ranking footballers by the probability of an internet search for their name leading to an unsafe website, with Ronaldo's name first on the list.

Ronaldo has been the subject of several works. His autobiography, titled "Moments", was published in December 2007. His sponsor Castrol produced the television film "Ronaldo: Tested to the Limit", in which he was physically and mentally tested in several areas; his physical performance was consequently subject to scrutiny by world media upon the film's release in September 2011. "", a documentary narrated by actor Benedict Cumberbatch, was released via Vimeo in June 2014. A documentary film directed by Anthony Wonke about his life and career, titled "Ronaldo", was released on 9 November 2015.

Demand for a replica Ronaldo shirt has been high throughout his career. In 2008, Ronaldo's number 7 Manchester United shirt was the best-selling Premier League sports product. In 2015, Ronaldo's number 7 Real Madrid shirt was the second best-selling worldwide, after Messi's number 10 Barcelona shirt. In 2018, within 24 hours of his number 7 Juventus shirt being released, over 520,000 had been sold, with $62.4 million generated in one day.

Ronaldo opened a fashion boutique under the name "CR7" (his initials and shirt number) on the island of Madeira in 2006 and opened a second in Lisbon in 2008. In partnership with Scandinavian manufacturer JBS Textile Group and the New York fashion designer Richard Chai, Ronaldo co-designed a range of underwear and sock line, released in November 2013. He expanded his "CR7" fashion brand by launching a line of premium shirts and shoes in July 2014. In September 2015, Ronaldo released his own fragrance, "Legacy", in a partnership with Eden Parfums.

In 2007, C.D. Nacional renamed its youth campus Cristiano Ronaldo Campus Futebol (Cristiano Ronaldo Football Campus). In December 2013, Ronaldo opened a museum, Museu CR7, in his hometown of Funchal, Madeira, to house trophies and memorabilia; the museum is an official sponsor of the local football team União da Madeira. At a ceremony held at the Belém Palace in January 2014, President of Portugal Aníbal Cavaco Silva raised Ronaldo to the rank of Grand Officer of the Order of Prince Henry "to distinguish an athlete of world renown who has been a symbol of Portugal globally, contributing to the international projection of the country and setting an example of tenacity for future generations." A bronze statue of Ronaldo, designed by artist Ricardo Madeira Veloso, was unveiled in Funchal on 21 December 2014.

In June 2010, during the build-up to the World Cup, Ronaldo became the fourth footballer (after Steven Gerrard, Pelé, and David Beckham) to be represented as a waxwork at Madame Tussauds London. Another waxwork of him was presented at the Madrid Wax Museum in December 2013. In June 2015, astronomers led by David Sobral from Lisbon and Leiden discovered a galaxy which they named Cosmos Redshift 7 (CR7) in tribute to Ronaldo.

On 23 July 2016, following Portugal's triumph at Euro 2016, Madeira Airport in Funchal was renamed as Cristiano Ronaldo International Airport. The unveiling of the rebranded terminal took place on 29 March 2017, which included a bust of his head being presented. The bust and the name change were controversial, with the lack of the bust's likeness to Ronaldo being ridiculed by comedians, including "Saturday Night Live", while the name change was subject to much debate locally by some politicians and citizens, who even started a petition against the move, an action criticised by President of Madeira Miguel Albuquerque. A year later, sports website Bleacher Report commissioned sculptor Emanuel Santos to create another bust; however, this bust was never used and a new one was made by a Spanish sculptor, shown to the public on 15 June 2018.

Ronaldo has had six children. He first became a father to a son, who was born on 17 June 2010 in the United States. He has full custody of the child and has not publicly revealed the identity of the mother per an agreement with her. In January 2015, Ronaldo's five-year relationship with Russian model Irina Shayk ended.

Ronaldo became a father to twins, born on 8 June 2017 in the United States via surrogacy. He is currently in a relationship with Argentine-born Spanish model Georgina Rodríguez, who gave birth to a daughter on 12 November 2017. The couple expected their second pair of twins in 2022. The male twin died during childbirth while the female twin survived. Ronaldo and his family are Roman Catholic.

Ronaldo's father, José, died of an alcoholism-related liver condition at age 52 in September 2005 when Ronaldo was 20.

Ronaldo has said that he does not drink alcohol, and he received libel damages over a "Daily Mirror" article that reported him drinking heavily in a nightclub while recovering from an injury in July 2008. He also does not have any tattoos as he regularly donates blood and bone marrow.

Ronaldo has made contributions to various charitable causes throughout his career. Television footage of the 2004 Indian Ocean earthquake and tsunami showed an eight-year-old boy survivor named Martunis wearing a Portuguese football shirt who was stranded for 19 days after his family was killed. Following this, Ronaldo visited Aceh, Indonesia, to raise funds for rehabilitation and reconstruction. After accepting undisclosed damages from a libel case against "The Sun" newspaper in 2008, Ronaldo donated the damages to a charity in Madeira. In 2009, Ronaldo donated £100,000 to the hospital that saved his mother's life in Madeira following her battle with cancer, so that they could build a cancer centre on the island. In support of the victims of the 2010 Madeira flood, Ronaldo pledged to play in a charity match in Madeira between Primeira Liga club Porto and players from Madeiran-based clubs Marítimo and Nacional.

In 2012, Ronaldo and his agent paid for specialist treatment for a nine-year-old Canarian boy with apparently terminal cancer. In December 2012, Ronaldo joined FIFA's "11 for Health" programme to raise awareness amongst kids of how to steer clear of conditions including drug addiction, HIV, malaria, and obesity. In January 2013, Ronaldo became Save the Children's new Global Artist Ambassador, in which he hopes to help fight child hunger and obesity. In March 2013, Ronaldo agreed to be the ambassador for The Mangrove Care Forum in Indonesia, an organisation aiming to raise awareness of mangrove conservation.

Ronaldo was named the world's most charitable sportsperson in 2015 after donating £5 million to the relief effort after the earthquake in Nepal which killed over 8,000 people. In June 2016, Ronaldo donated the entirety of his €600,000 Champions League bonus after Real Madrid won the competition. In August, Ronaldo launched CR7Selfie, a selfie app for charity to help Save the Children that lets participants take a selfie with him in one of several different outfits and poses.

In July 2017, Ronaldo was charged with fraudulently evading almost €15 million in tax between 2011 and 2014, a claim he denied at the time. In June 2018, Ronaldo was given a two-year suspended jail sentence and fined €18.8 million, later reduced to €16.8 million after reaching a deal with Spanish authorities. The sentence can be served under probation, without any jail time, so long as he does not re-offend.

Ronaldo and another man were investigated by the British Crown Prosecution Service after a 2005 rape allegation was brought forward by two women. Within days, the two women withdrew their allegation and Scotland Yard later issued a statement declaring there was not enough evidence for a prosecution.

In April 2017, it was reported that Ronaldo was being investigated by the Las Vegas Police Department for an allegation by a woman that he had raped her in 2009. Documents, confirmed by Ronaldo's lawyers, state that Ronaldo paid a woman US$375,000 in a non-disclosure settlement. Ronaldo and his lawyers issued a lengthy statement denying all accusations, describing them as an "intentional defamation campaign" with parts significantly "altered and/or completely fabricated", a claim which "Der Spiegel" categorically denied. In July 2019, Las Vegas prosecutors said they would not charge Ronaldo over allegations of rape; the statement added: "Based upon a review of information at this time, the allegations of sexual assault against Cristiano Ronaldo cannot be proven beyond a reasonable doubt." The same woman, in September 2018, filed a civil lawsuit in Nevada accusing Ronaldo of rape. "The Daily Mirror", citing court documents, reported in 2021 that the woman sought £56 million in damages from Ronaldo. In October 2021, federal magistrate judge Daniel Albregts recommended that the lawsuit be dismissed, citing that the woman's lawyer, Leslie Stovall, "acted in bad faith by asking for, receiving, and using Football Leaks documents to prosecute" the case, despite the documents containing "privileged communications" between Ronaldo and his lawyers. Additionally, Albregts stated that no evidence was found of Ronaldo's lawyers having "intimidated [the woman] or impeded law enforcement" during the 2010 settlement with her. In June 2022, the woman's rape lawsuit was dismissed with prejudice in the United States District Court for the District of Nevada, as district judge Jennifer A. Dorsey ruled that Stovall's repeated use of "cyber-hacked attorney-client privileged documents" were actions representing "abuses and flagrant circumvention of the proper litigation process".

Cleopatra VII Philopator (, "Cleopatra the father-beloved"; 69 BC10 August 30 BC) was Queen of the Ptolemaic Kingdom of Egypt from 51 to 30 BC, and its last active ruler. A member of the Ptolemaic dynasty, she was a descendant of its founder Ptolemy I Soter, a Macedonian Greek general and companion of Alexander the Great. After the death of Cleopatra, Egypt became a province of the Roman Empire, marking the end of the second to last Hellenistic state and the age that had lasted since the reign of Alexander (336–323 BC). Her native language was Koine Greek, and she was the only Ptolemaic ruler to learn the Egyptian language.

In 58 BC, Cleopatra presumably accompanied her father, Ptolemy XII Auletes, during his exile to Rome after a revolt in Egypt (a Roman client state) allowed his rival daughter Berenice IV to claim his throne. Berenice was killed in 55 BC when Ptolemy returned to Egypt with Roman military assistance. When he died in 51 BC, the joint reign of Cleopatra and her brother Ptolemy XIII began, but a falling-out between them led to open civil war. After losing the 48 BC Battle of Pharsalus in Greece against his rival Julius Caesar (a Roman dictator and consul) in Caesar's Civil War, the Roman statesman Pompey fled to Egypt. Pompey had been a political ally of Ptolemy XII, but Ptolemy XIII, at the urging of his court eunuchs, had Pompey ambushed and killed before Caesar arrived and occupied Alexandria. Caesar then attempted to reconcile the rival Ptolemaic siblings, but Ptolemy's chief adviser, Potheinos, viewed Caesar's terms as favoring Cleopatra, so his forces besieged her and Caesar at the palace. Shortly after the siege was lifted by reinforcements, Ptolemy XIII died in the 47 BC Battle of the Nile; Cleopatra's half-sister Arsinoe IV was eventually exiled to Ephesus for her role in carrying out the siege. Caesar declared Cleopatra and her brother Ptolemy XIV joint rulers but maintained a private affair with Cleopatra that produced a son, Caesarion. Cleopatra traveled to Rome as a client queen in 46 and 44 BC, where she stayed at Caesar's villa. After the assassinations of Caesar and (on her orders) Ptolemy XIV in 44 BC, she named Caesarion co-ruler as Ptolemy XV.

In the Liberators' civil war of 43–42 BC, Cleopatra sided with the Roman Second Triumvirate formed by Caesar's grandnephew and heir Octavian, Mark Antony, and Marcus Aemilius Lepidus. After their meeting at Tarsos in 41 BC, the queen had an affair with Antony. He carried out the execution of Arsinoe at her request, and became increasingly reliant on Cleopatra for both funding and military aid during his invasions of the Parthian Empire and the Kingdom of Armenia. The Donations of Alexandria declared their children Alexander Helios, Cleopatra Selene II, and Ptolemy Philadelphus rulers over various erstwhile territories under Antony's triumviral authority. This event, their marriage, and Antony's divorce of Octavian's sister Octavia Minor led to the final war of the Roman Republic. Octavian engaged in a war of propaganda, forced Antony's allies in the Roman Senate to flee Rome in 32 BC, and declared war on Cleopatra. After defeating Antony and Cleopatra's naval fleet at the 31 BC Battle of Actium, Octavian's forces invaded Egypt in 30 BC and defeated Antony, leading to Antony's suicide. When Cleopatra learned that Octavian planned to bring her to his Roman triumphal procession, she killed herself by poisoning, contrary to the popular belief that she was bitten by an asp.

Cleopatra's legacy survives in ancient and modern works of art. Roman historiography and Latin poetry produced a generally critical view of the queen that pervaded later Medieval and Renaissance literature. In the visual arts, her ancient depictions include Roman busts, paintings, and sculptures, cameo carvings and glass, Ptolemaic and Roman coinage, and reliefs. In Renaissance and Baroque art, she was the subject of many works including operas, paintings, poetry, sculptures, and theatrical dramas. She has become a pop culture icon of Egyptomania since the Victorian era, and in modern times, Cleopatra has appeared in the applied and fine arts, burlesque satire, Hollywood films, and brand images for commercial products.

The Latinized form Cleopatra comes from the Ancient Greek (), meaning "glory of her father", from (, "glory") and (, "father"). The masculine form would have been written either as () or (). Cleopatra was the name of Alexander the Great's sister, as well as Cleopatra Alcyone, wife of Meleager in Greek mythology. Through the marriage of Ptolemy V Epiphanes and Cleopatra I Syra (a Seleucid princess), the name entered the Ptolemaic dynasty. Cleopatra's adopted title () means "goddess who loves her father".

Ptolemaic pharaohs were crowned by the Egyptian high priest of Ptah at Memphis, but resided in the multicultural and largely Greek city of Alexandria, established by Alexander the Great of Macedon. They spoke Greek and governed Egypt as Hellenistic Greek monarchs, refusing to learn the native Egyptian language. In contrast, Cleopatra could speak multiple languages by adulthood and was the first Ptolemaic ruler to learn the Egyptian language. Plutarch implies that she also spoke Ethiopian, the language of the "Troglodytes", Hebrew (or Aramaic), Arabic, the Syrian language (perhaps Syriac), Median, and Parthian, and she could apparently also speak Latin, although her Roman contemporaries would have preferred to speak with her in her native Koine Greek. Aside from Greek, Egyptian, and Latin, these languages reflected Cleopatra's desire to restore North African and West Asian territories that once belonged to the Ptolemaic Kingdom.

Roman interventionism in Egypt predated the reign of Cleopatra. When Ptolemy IX Lathyros died in late 81 BC, he was succeeded by his daughter Berenice III. However, with opposition building at the royal court against the idea of a sole reigning female monarch, Berenice III accepted joint rule and marriage with her cousin and stepson Ptolemy XI Alexander II, an arrangement made by the Roman dictator Sulla. Ptolemy XI had his wife killed shortly after their marriage in 80 BC, but was lynched soon thereafter in the resulting riot over the assassination. Ptolemy XI, and perhaps his uncle Ptolemy IX or father Ptolemy X Alexander I, willed the Ptolemaic Kingdom to Rome as collateral for loans, so that the Romans had legal grounds to take over Egypt, their client state, after the assassination of Ptolemy XI. The Romans chose instead to divide the Ptolemaic realm among the illegitimate sons of Ptolemy IX, bestowing Cyprus on Ptolemy of Cyprus and Egypt on Ptolemy XII Auletes.

Cleopatra VII was born in early 69 BC to the ruling Ptolemaic pharaoh Ptolemy XII and an unknown mother, presumably Ptolemy XII's wife Cleopatra VI Tryphaena (also known as Cleopatra V Tryphaena), the mother of Cleopatra's older sister, Berenice IV Epiphaneia. Cleopatra Tryphaena disappears from official records a few months after the birth of Cleopatra in 69 BC. The three younger children of Ptolemy XII, Cleopatra's sister Arsinoe IV and brothers Ptolemy XIII Theos Philopator and Ptolemy XIV, were born in the absence of his wife. Cleopatra's childhood tutor was Philostratos, from whom she learned the Greek arts of oration and philosophy. During her youth Cleopatra presumably studied at the Musaeum, including the Library of Alexandria.

In 65 BC the Roman censor Marcus Licinius Crassus argued before the Roman Senate that Rome should annex Ptolemaic Egypt, but his proposed bill and the similar bill of tribune Servilius Rullus in 63 BC were rejected. Ptolemy XII responded to the threat of possible annexation by offering remuneration and lavish gifts to powerful Roman statesmen, such as Pompey during his campaign against Mithridates VI of Pontus, and eventually Julius Caesar after he became Roman consul in 59 BC. However, Ptolemy XII's profligate behavior bankrupted him, and he was forced to acquire loans from the Roman banker Gaius Rabirius Postumus.

In 58 BC the Romans annexed Cyprus and on accusations of piracy drove Ptolemy of Cyprus, Ptolemy XII's brother, to commit suicide instead of enduring exile to Paphos. Ptolemy XII remained publicly silent on the death of his brother, a decision which, along with ceding traditional Ptolemaic territory to the Romans, damaged his credibility among subjects already enraged by his economic policies. Ptolemy XII was then exiled from Egypt by force, traveling first to Rhodes, then Athens, and finally the villa of triumvir Pompey in the Alban Hills, near Praeneste, Italy. Ptolemy XII spent nearly a year there on the outskirts of Rome, ostensibly accompanied by his daughter Cleopatra, then about 11. Berenice IV sent an embassy to Rome to advocate for her rule and oppose the reinstatement of her father Ptolemy XII, but Ptolemy had assassins kill the leaders of the embassy, an incident that was covered up by his powerful Roman supporters. When the Roman Senate denied Ptolemy XII the offer of an armed escort and provisions for a return to Egypt, he decided to leave Rome in late 57 BC and reside at the Temple of Artemis in Ephesus.

The Roman financiers of Ptolemy XII remained determined to restore him to power. Pompey persuaded Aulus Gabinius, the Roman governor of Syria, to invade Egypt and restore Ptolemy XII, offering him 10,000 talents for the proposed mission. Although it put him at odds with Roman law, Gabinius invaded Egypt in the spring of 55 BC by way of Hasmonean Judea, where Hyrcanus II had Antipater the Idumaean, father of Herod the Great, furnish the Roman-led army with supplies. As a young cavalry officer, Mark Antony was under Gabinius's command. He distinguished himself by preventing Ptolemy XII from massacring the inhabitants of Pelousion, and for rescuing the body of Archelaos, the husband of Berenice IV, after he was killed in battle, ensuring him a proper royal burial. Cleopatra, then 14 years of age, would have traveled with the Roman expedition into Egypt; years later, Antony would profess that he had fallen in love with her at this time.

Gabinius was put on trial in Rome for abusing his authority, for which he was acquitted, but his second trial for accepting bribes led to his exile, from which he was recalled seven years later in 48 BC by Caesar. Crassus replaced him as governor of Syria and extended his provincial command to Egypt, but he was killed by the Parthians at the Battle of Carrhae in 53 BC. Ptolemy XII had Berenice IV and her wealthy supporters executed, seizing their properties. He allowed Gabinius's largely Germanic and Gallic Roman garrison, the Gabiniani, to harass people in the streets of Alexandria and installed his longtime Roman financier Rabirius as his chief financial officer. Within a year Rabirius was placed under protective custody and sent back to Rome after his life was endangered for draining Egypt of its resources. Despite these problems, Ptolemy XII created a will designating Cleopatra and Ptolemy XIII as his joint heirs, oversaw major construction projects such as the Temple of Edfu and a temple at Dendera, and stabilized the economy. On 31 May 52 BC, Cleopatra was made a regent of Ptolemy XII, as indicated by an inscription in the Temple of Hathor at Dendera. Rabirius was unable to collect the entirety of Ptolemy XII's debt by the time of the latter's death, and so it was passed on to his successors Cleopatra and Ptolemy XIII.

Ptolemy XII died sometime before 22 March 51 BC, when Cleopatra, in her first act as queen, began her voyage to Hermonthis, near Thebes, to install a new sacred Buchis bull, worshiped as an intermediary for the god Montu in the Ancient Egyptian religion. Cleopatra faced several pressing issues and emergencies shortly after taking the throne. These included famine caused by drought and a low level of the annual flooding of the Nile, and lawless behavior instigated by the Gabiniani, the now unemployed and assimilated Roman soldiers left by Gabinius to garrison Egypt. Inheriting her father's debts, Cleopatra also owed the Roman Republic 17.5 million drachmas.

In 50 BC Marcus Calpurnius Bibulus, proconsul of Syria, sent his two eldest sons to Egypt, most likely to negotiate with the Gabiniani and recruit them as soldiers in the desperate defense of Syria against the Parthians. However, the Gabiniani tortured and murdered these two, perhaps with secret encouragement by rogue senior administrators in Cleopatra's court. Cleopatra sent the Gabiniani culprits to Bibulus as prisoners awaiting his judgment, but he sent them back to Cleopatra and chastised her for interfering in their adjudication, which was the prerogative of the Roman Senate. Bibulus, siding with Pompey in Caesar's Civil War, failed to prevent Caesar from landing a naval fleet in Greece, which ultimately allowed Caesar to reach Egypt in pursuit of Pompey.

By 29 August 51 BC, official documents started listing Cleopatra as the sole ruler, evidence that she had rejected her brother Ptolemy XIII as a co-ruler. She had probably married him, but there is no record of this. The Ptolemaic practice of sibling marriage was introduced by Ptolemy II and his sister Arsinoe II. A long-held royal Egyptian practice, it was loathed by contemporary Greeks. By the reign of Cleopatra, however, it was considered a normal arrangement for Ptolemaic rulers.

Despite Cleopatra's rejection of him, Ptolemy XIII still retained powerful allies, notably the eunuch Potheinos, his childhood tutor, regent, and administrator of his properties. Others involved in the cabal against Cleopatra included Achillas, a prominent military commander, and Theodotus of Chios, another tutor of Ptolemy XIII. Cleopatra seems to have attempted a short-lived alliance with her brother Ptolemy XIV, but by the autumn of 50 BC Ptolemy XIII had the upper hand in their conflict and began signing documents with his name before that of his sister, followed by the establishment of his first regnal date in 49 BC.

In the summer of 49 BC, Cleopatra and her forces were still fighting against Ptolemy XIII within Alexandria when Pompey's son Gnaeus Pompeius arrived, seeking military aid on behalf of his father. After returning to Italy from the wars in Gaul and crossing the Rubicon in January of 49 BC, Caesar had forced Pompey and his supporters to flee to Greece. In perhaps their last joint decree, both Cleopatra and Ptolemy XIII agreed to Gnaeus Pompeius's request and sent his father 60 ships and 500 troops, including the Gabiniani, a move that helped erase some of the debt owed to Rome. Losing the fight against her brother, Cleopatra was then forced to flee Alexandria and withdraw to the region of Thebes. By the spring of 48 BC Cleopatra had traveled to Roman Syria with her younger sister, Arsinoe IV, to gather an invasion force that would head to Egypt. She returned with an army, but her advance to Alexandria was blocked by her brother's forces, including some Gabiniani mobilized to fight against her, so she camped outside Pelousion in the eastern Nile Delta.

In Greece, Caesar and Pompey's forces engaged each other at the decisive Battle of Pharsalus on 9August 48 BC, leading to the destruction of most of Pompey's army and his forced flight to Tyre, Lebanon. Given his close relationship with the Ptolemies, Pompey ultimately decided that Egypt would be his place of refuge, where he could replenish his forces. Ptolemy XIII's advisers, however, feared the idea of Pompey using Egypt as his base in a protracted Roman civil war. In a scheme devised by Theodotus, Pompey arrived by ship near Pelousion after being invited by a written message, only to be ambushed and stabbed to death on 28 September 48 BC. Ptolemy XIII believed he had demonstrated his power and simultaneously defused the situation by having Pompey's head, severed and embalmed, sent to Caesar, who arrived in Alexandria by early October and took up residence at the royal palace. Caesar expressed grief and outrage over the killing of Pompey and called on both Ptolemy XIII and Cleopatra to disband their forces and reconcile with each other.

Ptolemy XIII arrived at Alexandria at the head of his army, in clear defiance of Caesar's demand that he disband and leave his army before his arrival. Cleopatra initially sent emissaries to Caesar, but upon allegedly hearing that Caesar was inclined to having affairs with royal women, she came to Alexandria to see him personally. Historian Cassius Dio records that she did so without informing her brother, dressed in an attractive manner, and charmed Caesar with her wit. Plutarch provides an entirely different and perhaps mythical account that alleges she was bound inside a bed sack to be smuggled into the palace to meet Caesar.

When Ptolemy XIII realized that his sister was in the palace consorting directly with Caesar, he attempted to rouse the populace of Alexandria into a riot, but he was arrested by Caesar, who used his oratorical skills to calm the frenzied crowd. Caesar then brought Cleopatra and Ptolemy XIII before the assembly of Alexandria, where Caesar revealed the written will of Ptolemy XII—previously possessed by Pompey—naming Cleopatra and Ptolemy XIII as his joint heirs. Caesar then attempted to arrange for the other two siblings, Arsinoe IV and Ptolemy XIV, to rule together over Cyprus, thus removing potential rival claimants to the Egyptian throne while also appeasing the Ptolemaic subjects still bitter over the loss of Cyprus to the Romans in 58 BC.

Judging that this agreement favored Cleopatra over Ptolemy XIII and that the latter's army of 20,000, including the Gabiniani, could most likely defeat Caesar's army of 4,000 unsupported troops, Potheinos decided to have Achillas lead their forces to Alexandria to attack both Caesar and Cleopatra. After Caesar managed to execute Potheinos, Arsinoe IV joined forces with Achillas and was declared queen, but soon afterward had her tutor Ganymedes kill Achillas and take his position as commander of her army. Ganymedes then tricked Caesar into requesting the presence of the erstwhile captive Ptolemy XIII as a negotiator, only to have him join the army of Arsinoe IV. The resulting siege of the palace, with Caesar and Cleopatra trapped together inside, lasted into the following year of 47 BC.

Sometime between January and March of 47 BC, Caesar's reinforcements arrived, including those led by Mithridates of Pergamon and Antipater the Idumaean. Ptolemy XIII and Arsinoe IV withdrew their forces to the Nile, where Caesar attacked them. Ptolemy XIII tried to flee by boat, but it capsized, and he drowned. Ganymedes may have been killed in the battle. Theodotus was found years later in Asia, by Marcus Junius Brutus, and executed. Arsinoe IV was forcefully paraded in Caesar's triumph in Rome before being exiled to the Temple of Artemis at Ephesus. Cleopatra was conspicuously absent from these events and resided in the palace, most likely because she had been pregnant with Caesar's child since September 48 BC.

Caesar's term as consul had expired at the end of 48 BC. However, Antony, an officer of his, helped to secure Caesar's appointment as dictator lasting for a year, until October 47 BC, providing Caesar with the legal authority to settle the dynastic dispute in Egypt. Wary of repeating the mistake of Cleopatra's sister Berenice IV in having a female monarch as sole ruler, Caesar appointed Cleopatra's 12-year-old brother, Ptolemy XIV, as joint ruler with the 22-year-old Cleopatra in a nominal sibling marriage, but Cleopatra continued living privately with Caesar. The exact date at which Cyprus was returned to her control is not known, although she had a governor there by 42 BC.

Caesar is alleged to have joined Cleopatra for a cruise of the Nile and sightseeing of Egyptian monuments, although this may be a romantic tale reflecting later well-to-do Roman proclivities and not a real historical event. The historian Suetonius provided considerable details about the voyage, including use of "Thalamegos", the pleasure barge constructed by Ptolemy IV, which during his reign measured in length and in height and was complete with dining rooms, state rooms, holy shrines, and promenades along its two decks, resembling a floating villa. Caesar could have had an interest in the Nile cruise owing to his fascination with geography; he was well-read in the works of Eratosthenes and Pytheas, and perhaps wanted to discover the source of the river, but turned back before reaching Ethiopia.

Caesar departed from Egypt around April 47 BC, allegedly to confront Pharnaces II of Pontus, the son of Mithridates VI of Pontus, who was stirring up trouble for Rome in Anatolia. It is possible that Caesar, married to the prominent Roman woman Calpurnia, also wanted to avoid being seen together with Cleopatra when she bore him their son. He left three legions in Egypt, later increased to four, under the command of the freedman Rufio, to secure Cleopatra's tenuous position, but also perhaps to keep her activities in check.

Caesarion, Cleopatra's alleged child with Caesar, was born 23 June 47 BC and was originally named "Pharaoh Caesar", as preserved on a stele at the Serapeum of Saqqara. Perhaps owing to his still childless marriage with Calpurnia, Caesar remained publicly silent about Caesarion (but perhaps accepted his parentage in private). Cleopatra, on the other hand, made repeated official declarations about Caesarion's parentage, naming Caesar as the father.

Cleopatra and her nominal joint ruler Ptolemy XIV visited Rome sometime in late 46 BC, presumably without Caesarion, and were given lodging in Caesar's villa within the Horti Caesaris. As with their father Ptolemy XII, Caesar awarded both Cleopatra and Ptolemy XIV the legal status of "friend and ally of the Roman people" (), in effect client rulers loyal to Rome. Cleopatra's visitors at Caesar's villa across the Tiber included the senator Cicero, who found her arrogant. Sosigenes of Alexandria, one of the members of Cleopatra's court, aided Caesar in the calculations for the new Julian calendar, put into effect 1January 45 BC. The Temple of Venus Genetrix, established in the Forum of Caesar on 25 September 46 BC, contained a golden statue of Cleopatra (which stood there at least until the 3rd century AD), associating the mother of Caesar's child directly with the goddess Venus, mother of the Romans. The statue also subtly linked the Egyptian goddess Isis with the Roman religion.

Cleopatra's presence in Rome most likely had an effect on the events at the Lupercalia festival a month before Caesar's assassination. Antony attempted to place a royal diadem on Caesar's head, but the latter refused in what was most likely a staged performance, perhaps to gauge the Roman public's mood about accepting Hellenistic-style kingship. Cicero, who was present at the festival, mockingly asked where the diadem came from, an obvious reference to the Ptolemaic queen whom he abhorred. Caesar was assassinated on the Ides of March (15 March 44 BC), but Cleopatra stayed in Rome until about mid-April, in the vain hope of having Caesarion recognized as Caesar's heir. However, Caesar's will named his grandnephew Octavian as the primary heir, and Octavian arrived in Italy around the same time Cleopatra decided to depart for Egypt. A few months later, Cleopatra had Ptolemy XIV killed by poisoning, elevating her son Caesarion as her co-ruler.

Octavian, Antony, and Marcus Aemilius Lepidus formed the Second Triumvirate in 43 BC, in which they were each elected for five-year terms to restore order in the Republic and bring Caesar's assassins to justice. Cleopatra received messages from both Gaius Cassius Longinus, one of Caesar's assassins, and Publius Cornelius Dolabella, proconsul of Syria and Caesarian loyalist, requesting military aid. She decided to write Cassius an excuse that her kingdom faced too many internal problems, while sending the four legions left by Caesar in Egypt to Dolabella. However, these troops were captured by Cassius in Palestine. While Serapion, Cleopatra's governor of Cyprus, defected to Cassius and provided him with ships, Cleopatra took her own fleet to Greece to personally assist Octavian and Antony, but her ships were heavily damaged in a Mediterranean storm and she arrived too late to aid in the fighting. By the autumn of 42 BC, Antony had defeated the forces of Caesar's assassins at the Battle of Philippi in Greece, leading to the suicide of Cassius and Brutus.

By the end of 42 BC, Octavian had gained control over much of the western half of the Roman Republic and Antony the eastern half, with Lepidus largely marginalized. In the summer of 41 BC, Antony established his headquarters at Tarsos in Anatolia and summoned Cleopatra there in several letters, which she rebuffed until Antony's envoy Quintus Dellius convinced her to come. The meeting would allow Cleopatra to clear up the misconception that she had supported Cassius during the civil war and address territorial exchanges in the Levant, but Antony also undoubtedly desired to form a personal, romantic relationship with the queen. Cleopatra sailed up the Kydnos River to Tarsos in "Thalamegos", hosting Antony and his officers for two nights of lavish banquets on board the ship. Cleopatra managed to clear her name as a supposed supporter of Cassius, arguing she had really attempted to help Dolabella in Syria, and convinced Antony to have her exiled sister, Arsinoe IV, executed at Ephesus. Cleopatra's former rebellious governor of Cyprus was also handed over to her for execution.

Cleopatra invited Antony to come to Egypt before departing from Tarsos, which led Antony to visit Alexandria by November 41 BC. Antony was well received by the populace of Alexandria, both for his heroic actions in restoring Ptolemy XII to power and coming to Egypt without an occupation force like Caesar had done. In Egypt, Antony continued to enjoy the lavish royal lifestyle he had witnessed aboard Cleopatra's ship docked at Tarsos. He also had his subordinates, such as Publius Ventidius Bassus, drive the Parthians out of Anatolia and Syria.

Cleopatra carefully chose Antony as her partner for producing further heirs, as he was deemed to be the most powerful Roman figure following Caesar's demise. With his powers as a triumvir, Antony also had the broad authority to restore former Ptolemaic lands, which were currently in Roman hands, to Cleopatra. While it is clear that both Cilicia and Cyprus were under Cleopatra's control by 19 November 38 BC, the transfer probably occurred earlier in the winter of 41–40 BC, during her time spent with Antony.

By the spring of 40 BC, Antony left Egypt due to troubles in Syria, where his governor Lucius Decidius Saxa was killed and his army taken by Quintus Labienus, a former officer under Cassius who now served the Parthian Empire. Cleopatra provided Antony with 200 ships for his campaign and as payment for her newly acquired territories. She would not see Antony again until 37 BC, but she maintained correspondence, and evidence suggests she kept a spy in his camp. By the end of 40 BC, Cleopatra had given birth to twins, a boy named Alexander Helios and a girl named Cleopatra Selene II, both of whom Antony acknowledged as his children. Helios (the Sun) and Selene (the Moon) were symbolic of a new era of societal rejuvenation, as well as an indication that Cleopatra hoped Antony would repeat the exploits of Alexander the Great by conquering the Parthians.

Mark Antony's Parthian campaign in the east was disrupted by the events of the Perusine War (41–40 BC), initiated by his ambitious wife Fulvia against Octavian in the hopes of making her husband the undisputed leader of Rome. It has been suggested that Fulvia wanted to cleave Antony away from Cleopatra, but the conflict emerged in Italy even before Cleopatra's meeting with Antony at Tarsos. Fulvia and Antony's brother Lucius Antonius were eventually besieged by Octavian at Perusia (modern Perugia, Italy) and then exiled from Italy, after which Fulvia died at Sicyon in Greece while attempting to reach Antony. Her sudden death led to a reconciliation of Octavian and Antony at Brundisium in Italy in September 40 BC. Although the agreement struck at Brundisium solidified Antony's control of the Roman Republic's territories east of the Ionian Sea, it also stipulated that he concede Italia, Hispania, and Gaul, and marry Octavian's sister Octavia the Younger, a potential rival for Cleopatra.

In December 40 BC Cleopatra received Herod in Alexandria as an unexpected guest and refugee who fled a turbulent situation in Judea. Herod had been installed as a tetrarch there by Antony, but he was soon at odds with Antigonus II Mattathias of the long-established Hasmonean dynasty. The latter had imprisoned Herod's brother and fellow tetrarch Phasael, who was executed while Herod was fleeing toward Cleopatra's court. Cleopatra attempted to provide him with a military assignment, but Herod declined and traveled to Rome, where the triumvirs Octavian and Antony named him king of Judea. This act put Herod on a collision course with Cleopatra, who would desire to reclaim the former Ptolemaic territories that comprised his new Herodian kingdom.

Relations between Antony and Cleopatra perhaps soured when he not only married Octavia, but also sired her two children, Antonia the Elder in 39 BC and Antonia Minor in 36 BC, and moved his headquarters to Athens. However, Cleopatra's position in Egypt was secure. Her rival Herod was occupied with civil war in Judea that required heavy Roman military assistance, but received none from Cleopatra. Since the authority of Antony and Octavian as triumvirs had expired on 1January 37 BC, Octavia arranged for a meeting at Tarentum, where the triumvirate was officially extended to 33 BC. With two legions granted by Octavian and a thousand soldiers lent by Octavia, Antony traveled to Antioch, where he made preparations for war against the Parthians.

Antony summoned Cleopatra to Antioch to discuss pressing issues, such as Herod's kingdom and financial support for his Parthian campaign. Cleopatra brought her now three-year-old twins to Antioch, where Antony saw them for the first time and where they probably first received their surnames Helios and Selene as part of Antony and Cleopatra's ambitious plans for the future. In order to stabilize the east, Antony not only enlarged Cleopatra's domain, he also established new ruling dynasties and client rulers who would be loyal to him, yet would ultimately outlast him.

In this arrangement Cleopatra gained significant former Ptolemaic territories in the Levant, including nearly all of Phoenicia (Lebanon) minus Tyre and Sidon, which remained in Roman hands. She also received Ptolemais Akko (modern Acre, Israel), a city that was established by Ptolemy II. Given her ancestral relations with the Seleucids, she was granted the region of Coele-Syria along the upper Orontes River. She was even given the region surrounding Jericho in Palestine, but she leased this territory back to Herod. At the expense of the Nabataean king Malichus I (a cousin of Herod), Cleopatra was also given a portion of the Nabataean Kingdom around the Gulf of Aqaba on the Red Sea, including Ailana (modern Aqaba, Jordan). To the west Cleopatra was handed Cyrene along the Libyan coast, as well as Itanos and Olous in Roman Crete. Although still administered by Roman officials, these territories nevertheless enriched her kingdom and led her to declare the inauguration of a new era by double-dating her coinage in 36 BC.

Antony's enlargement of the Ptolemaic realm by relinquishing directly controlled Roman territory was exploited by his rival Octavian, who tapped into the public sentiment in Rome against the empowerment of a foreign queen at the expense of their Republic. Octavian, fostering the narrative that Antony was neglecting his virtuous Roman wife Octavia, granted both her and Livia, his own wife, extraordinary privileges of sacrosanctity. Some 50 years before, Cornelia Africana, daughter of Scipio Africanus, had been the first living Roman woman to have a statue dedicated to her. She was now followed by Octavia and Livia, whose statues were most likely erected in the Forum of Caesar to rival that of Cleopatra's, erected by Caesar.

In 36 BC, Cleopatra accompanied Antony to the Euphrates in his journey toward invading the Parthian Empire. She then returned to Egypt, perhaps due to her advanced state of pregnancy. By the summer of 36 BC, she had given birth to Ptolemy Philadelphus, her second son with Antony.

Antony's Parthian campaign in 36 BC turned into a complete debacle for a number of reasons, in particular the betrayal of Artavasdes II of Armenia, who defected to the Parthian side. After losing some 30,000 men, more than Crassus at Carrhae (an indignity he had hoped to avenge), Antony finally arrived at Leukokome near Berytus (modern Beirut, Lebanon) in December, engaged in heavy drinking before Cleopatra arrived to provide funds and clothing for his battered troops. Antony desired to avoid the risks involved in returning to Rome, and so he traveled with Cleopatra back to Alexandria to see his newborn son.

As Antony prepared for another Parthian expedition in 35 BC, this time aimed at their ally Armenia, Octavia traveled to Athens with 2,000 troops in alleged support of Antony, but most likely in a scheme devised by Octavian to embarrass him for his military losses. Antony received these troops but told Octavia not to stray east of Athens as he and Cleopatra traveled together to Antioch, only to suddenly and inexplicably abandon the military campaign and head back to Alexandria. When Octavia returned to Rome Octavian portrayed his sister as a victim wronged by Antony, although she refused to leave Antony's household. Octavian's confidence grew as he eliminated his rivals in the west, including Sextus Pompeius and even Lepidus, the third member of the triumvirate, who was placed under house arrest after revolting against Octavian in Sicily.

Dellius was sent as Antony's envoy to Artavasdes II in 34 BC to negotiate a potential marriage alliance that would wed the Armenian king's daughter to Alexander Helios, the son of Antony and Cleopatra. When this was declined, Antony marched his army into Armenia, defeated their forces and captured the king and Armenian royal family. Antony then held a military parade in Alexandria as an imitation of a Roman triumph, dressed as Dionysus and riding into the city on a chariot to present the royal prisoners to Cleopatra, who was seated on a golden throne above a silver dais. News of this event was heavily criticized in Rome as a perversion of time-honored Roman rites and rituals to be enjoyed instead by an Egyptian queen.

In an event held at the gymnasium soon after the triumph, Cleopatra dressed as Isis and declared that she was the Queen of Kings with her son Caesarion, King of Kings, while Alexander Helios was declared king of Armenia, Media, and Parthia, and two-year-old Ptolemy Philadelphos was declared king of Syria and Cilicia. Cleopatra Selene II was bestowed with Crete and Cyrene. Antony and Cleopatra may have been wed during this ceremony. Antony sent a report to Rome requesting ratification of these territorial claims, now known as the Donations of Alexandria. Octavian wanted to publicize it for propaganda purposes, but the two consuls, both supporters of Antony, had it censored from public view.

In late 34 BC, Antony and Octavian engaged in a heated war of propaganda that would last for years. Antony claimed that his rival had illegally deposed Lepidus from their triumvirate and barred him from raising troops in Italy, while Octavian accused Antony of unlawfully detaining the king of Armenia, marrying Cleopatra despite still being married to his sister Octavia, and wrongfully claiming Caesarion as the heir of Caesar instead of Octavian. The litany of accusations and gossip associated with this propaganda war have shaped the popular perceptions about Cleopatra from Augustan-period literature through to various media in modern times. Cleopatra was said to have brainwashed Mark Antony with witchcraft and sorcery and was as dangerous as Homer's Helen of Troy in destroying civilization. Pliny the Elder claims in his "Natural History" that Cleopatra once dissolved a pearl worth tens of millions of sesterces in vinegar just to win a dinner-party bet. The accusation that Antony had stolen books from the Library of Pergamum to restock the Library of Alexandria later turned out to be an admitted fabrication by Gaius Calvisius Sabinus.

A papyrus document dated to February 33 BC, later used to wrap a mummy, contains the signature of Cleopatra, probably written by an official authorized to sign for her. It concerns certain tax exemptions in Egypt granted to either Quintus Caecillius or Publius Canidius Crassus, a former Roman consul and Antony's confidant who would command his land forces at Actium. A subscript in a different handwriting at the bottom of the papyrus reads "make it happen" or "so be it" (); this is likely the autograph of the queen, as it was Ptolemaic practice to countersign documents to avoid forgery.

In a speech to the Roman Senate on the first day of his consulship on 1January 33 BC, Octavian accused Antony of attempting to subvert Roman freedoms and territorial integrity as a slave to his Oriental queen. Before Antony and Octavian's joint "imperium" expired on 31 December 33 BC, Antony declared Caesarion as the true heir of Caesar in an attempt to undermine Octavian. In 32 BC, the Antonian loyalists Gaius Sosius and Gnaeus Domitius Ahenobarbus became consuls. The former gave a fiery speech condemning Octavian, now a private citizen without public office, and introduced pieces of legislation against him. During the next senatorial session, Octavian entered the Senate house with armed guards and levied his own accusations against the consuls. Intimidated by this act, the consuls and over 200 senators still in support of Antony fled Rome the next day to join the side of Antony.

Antony and Cleopatra traveled together to Ephesus in 32 BC, where she provided him with 200 of the 800 naval ships he was able to acquire. Ahenobarbus, wary of having Octavian's propaganda confirmed to the public, attempted to persuade Antony to have Cleopatra excluded from the campaign against Octavian. Publius Canidius Crassus made the counterargument that Cleopatra was funding the war effort and was a competent monarch. Cleopatra refused Antony's requests that she return to Egypt, judging that by blocking Octavian in Greece she could more easily defend Egypt. Cleopatra's insistence that she be involved in the battle for Greece led to the defections of prominent Romans, such as Ahenobarbus and Lucius Munatius Plancus.

During the spring of 32 BC Antony and Cleopatra traveled to Athens, where she persuaded Antony to send Octavia an official declaration of divorce. This encouraged Plancus to advise Octavian that he should seize Antony's will, invested with the Vestal Virgins. Although a violation of sacred and legal rights, Octavian forcefully acquired the document from the Temple of Vesta, and it became a useful tool in the propaganda war against Antony and Cleopatra. Octavian highlighted parts of the will, such as Caesarion being named heir to Caesar, that the Donations of Alexandria were legal, that Antony should be buried alongside Cleopatra in Egypt instead of Rome, and that Alexandria would be made the new capital of the Roman Republic. In a show of loyalty to Rome, Octavian decided to begin construction of his own mausoleum at the Campus Martius. Octavian's legal standing was also improved by being elected consul in 31 BC. With Antony's will made public, Octavian had his "casus belli", and Rome declared war on Cleopatra, not Antony. The legal argument for war was based less on Cleopatra's territorial acquisitions, with former Roman territories ruled by her children with Antony, and more on the fact that she was providing military support to a private citizen now that Antony's triumviral authority had expired.

Antony and Cleopatra had a larger fleet than Octavian, but the crews of Antony and Cleopatra's navy were not all well-trained, some of them perhaps from merchant vessels, whereas Octavian had a fully professional force. Antony wanted to cross the Adriatic Sea and blockade Octavian at either Tarentum or Brundisium, but Cleopatra, concerned primarily with defending Egypt, overrode the decision to attack Italy directly. Antony and Cleopatra set up their winter headquarters at Patrai in Greece, and by the spring of 31 BC they had moved to Actium, on the southern side of the Ambracian Gulf.

Cleopatra and Antony had the support of various allied kings, but Cleopatra had already been in conflict with Herod, and an earthquake in Judea provided him with an excuse to be absent from the campaign. They also lost the support of Malichus I, which would prove to have strategic consequences. Antony and Cleopatra lost several skirmishes against Octavian around Actium during the summer of 31 BC, while defections to Octavian's camp continued, including Antony's long-time companion Dellius and the allied kings Amyntas of Galatia and Deiotaros of Paphlagonia. While some in Antony's camp suggested abandoning the naval conflict to retreat inland, Cleopatra urged for a naval confrontation, to keep Octavian's fleet away from Egypt.

On 2 September 31 BC the naval forces of Octavian, led by Marcus Vipsanius Agrippa, met those of Antony and Cleopatra at the Battle of Actium. Cleopatra, aboard her flagship, the "Antonias", commanded 60 ships at the mouth of the Ambracian Gulf, at the rear of the fleet, in what was likely a move by Antony's officers to marginalize her during the battle. Antony had ordered that their ships should have sails on board for a better chance to pursue or flee from the enemy, which Cleopatra, ever concerned about defending Egypt, used to swiftly move through the area of major combat in a strategic withdrawal to the Peloponnese. Burstein writes that partisan Roman writers would later accuse Cleopatra of cowardly deserting Antony, but their original intention of keeping their sails on board may have been to break the blockade and salvage as much of their fleet as possible. Antony followed Cleopatra and boarded her ship, identified by its distinctive purple sails, as the two escaped the battle and headed for Tainaron. Antony reportedly avoided Cleopatra during this three-day voyage, until her ladies in waiting at Tainaron urged him to speak with her. The Battle of Actium raged on without Cleopatra and Antony until the morning of 3September, and was followed by massive defections of officers, troops, and allied kings to Octavian's side.

While Octavian occupied Athens, Antony and Cleopatra landed at Paraitonion in Egypt. The couple then went their separate ways, Antony to Cyrene to raise more troops and Cleopatra to the harbor at Alexandria in an attempt to mislead the oppositional party and portray the activities in Greece as a victory. She was afraid that news about the outcome of the battle of Actium would lead to a rebellion. It is uncertain whether or not, at this time, she actually executed Artavasdes II and sent his head to his rival, Artavasdes I of Media Atropatene, in an attempt to strike an alliance with him.

Lucius Pinarius, Mark Antony's appointed governor of Cyrene, received word that Octavian had won the Battle of Actium before Antony's messengers could arrive at his court. Pinarius had these messengers executed and then defected to Octavian's side, surrendering to him the four legions under his command that Antony desired to obtain. Antony nearly committed suicide after hearing news of this but was stopped by his staff officers. In Alexandria he built a reclusive cottage on the island of Pharos that he nicknamed the "Timoneion", after the philosopher Timon of Athens, who was famous for his cynicism and misanthropy. Herod, who had personally advised Antony after the Battle of Actium that he should betray Cleopatra, traveled to Rhodes to meet Octavian and resign his kingship out of loyalty to Antony. Octavian was impressed by his speech and sense of loyalty, so he allowed him to maintain his position in Judea, further isolating Antony and Cleopatra.

Cleopatra perhaps started to view Antony as a liability by the late summer of 31 BC, when she prepared to leave Egypt to her son Caesarion. Cleopatra planned to relinquish her throne to him, take her fleet from the Mediterranean into the Red Sea, and then set sail to a foreign port, perhaps in India, where she could spend time recuperating. However, these plans were ultimately abandoned when Malichus I, as advised by Octavian's governor of Syria, Quintus Didius, managed to burn Cleopatra's fleet in revenge for his losses in a war with Herod that Cleopatra had largely initiated. Cleopatra had no other option but to stay in Egypt and negotiate with Octavian. Although most likely later pro-Octavian propaganda, it was reported that at this time Cleopatra started testing the strengths of various poisons on prisoners and even her own servants.

Cleopatra had Caesarion enter into the ranks of the "ephebi", which, along with reliefs on a stele from Koptos dated 21 September 31 BC, demonstrated that Cleopatra was now grooming her son to become the sole ruler of Egypt. In a show of solidarity, Antony also had Marcus Antonius Antyllus, his son with Fulvia, enter the "ephebi" at the same time. Separate messages and envoys from Antony and Cleopatra were then sent to Octavian, still stationed at Rhodes, although Octavian seems to have replied only to Cleopatra. Cleopatra requested that her children should inherit Egypt and that Antony should be allowed to live in exile in Egypt, offered Octavian money in the future, and immediately sent him lavish gifts. Octavian sent his diplomat Thyrsos to Cleopatra after she threatened to burn herself and vast amounts of her treasure within a tomb already under construction. Thyrsos advised her to kill Antony so that her life would be spared, but when Antony suspected foul intent, he had this diplomat flogged and sent back to Octavian without a deal.

After lengthy negotiations that ultimately produced no results, Octavian set out to invade Egypt in the spring of 30 BC, stopping at Ptolemais in Phoenicia, where his new ally Herod provided his army with fresh supplies. Octavian moved south and swiftly took Pelousion, while Cornelius Gallus, marching eastward from Cyrene, defeated Antony's forces near Paraitonion. Octavian advanced quickly to Alexandria, but Antony returned and won a small victory over Octavian's tired troops outside the city's hippodrome. However, on 1 August 30 BC, Antony's naval fleet surrendered to Octavian, followed by Antony's cavalry. Cleopatra hid herself in her tomb with her close attendants and sent a message to Antony that she had committed suicide. In despair, Antony responded to this by stabbing himself in the stomach and taking his own life at age 53. According to Plutarch, he was still dying when brought to Cleopatra at her tomb, telling her he had died honorably and that she could trust Octavian's companion Gaius Proculeius over anyone else in his entourage. It was Proculeius, however, who infiltrated her tomb using a ladder and detained the queen, denying her the ability to burn herself with her treasures. Cleopatra was then allowed to embalm and bury Antony within her tomb before she was escorted to the palace.

Octavian entered Alexandria, occupied the palace, and seized Cleopatra's three youngest children. When she met with Octavian, Cleopatra told him bluntly, "I will not be led in a triumph" (), according to Livy, a rare recording of her exact words. Octavian promised that he would keep her alive but offered no explanation about his future plans for her kingdom. When a spy informed her that Octavian planned to move her and her children to Rome in three days, she prepared for suicide as she had no intentions of being paraded in a Roman triumph like her sister Arsinoe IV. It is unclear if Cleopatra's suicide on 10 August 30 BC, at age 39, took place within the palace or her tomb. It is said she was accompanied by her servants Eiras and Charmion, who also took their own lives. Octavian was said to have been angered by this outcome but had Cleopatra buried in royal fashion next to Antony in her tomb. Cleopatra's physician Olympos did not explain her cause of death, although the popular belief is that she allowed an asp or Egyptian cobra to bite and poison her. Plutarch relates this tale, but then suggests an implement (, ,  'spine, cheese-grater') was used to introduce the toxin by scratching, while Dio says that she injected the poison with a needle (, ), and Strabo argued for an ointment of some kind. No venomous snake was found with her body, but she did have tiny puncture wounds on her arm that could have been caused by a needle.

Cleopatra decided in her last moments to send Caesarion away to Upper Egypt, perhaps with plans to flee to Kushite Nubia, Ethiopia, or India. Caesarion, now Ptolemy XV, would reign for a mere 18 days until executed on the orders of Octavian on 29 August 30 BC, after returning to Alexandria under the false pretense that Octavian would allow him to be king. Octavian was convinced by the advice of the philosopher Arius Didymus that there was room for only one Caesar in the world. With the fall of the Ptolemaic Kingdom, the Roman province of Egypt was established, marking the end of the Hellenistic period. In January of 27 BC Octavian was renamed Augustus ("the revered") and amassed constitutional powers that established him as the first Roman emperor, inaugurating the Principate era of the Roman Empire.