# History of Southend United F.C.

Southend United F.C. is a professional football club formed in 1906 and based in Southend-on-Sea. Initially playing in the Southern League, the club joined the Football League in 1920 and then competed in the third tier of English football for most subsequent seasons. The side reached the second tier Championship level in the 1990s and again in the early 2000s, but by 2009 the club had major financial difficulties and narrowly avoided administration on several occasions. The financial problems continued through to the early 2020s, during which it was relegated from the Football League to the fifth tier National League, with the club subject to numerous winding-up petitions.

## History
### 1906–1958

Southend United F.C. was founded on 19 May 1906 in the Blue Boar Hotel after landlord Oliver Trigg invited a group of footballers and businessmen to discuss setting up a new professional club. A prospectus for shares in the club issued in August 1906 noted the club had been elected to complete in the Second Division of the Southern League and in the South Eastern League, and a seven-year lease had been agreed to play at Roots Hall Field in Prittlewell. Robert Jack ("late of Plymouth Argyle Football Club") was appointed as manager, secretary and player, and 12 professional players were recruited, including two - outside left Alfred Ernest Watkins (formerly at Millwall) and back George Molyneux (formerly at Portsmouth) - listed as internationals (Watkins had played for Wales, Molyneux for England). Other signings included goalkeeper Charles Cotton from West Ham, outside right Arthur Holden from Portsmouth, and centre-forward Harold Halse from Wanstead, plus players from Southend Athletic, Grays United, South Weald and Leigh Ramblers.
In their first season under Jack's management, Southend won the Southern League Second Division title for 1906–07, then repeated the feat the following season, gaining election to the Southern League First Division in 1908. When Jack left Southend in 1910, he was succeeded as player-manager by Molyneux. Southend were relegated back to the Second Division after the 1910–11 season, but returned to the First Division two seasons later.
The club remained in the Southern League until the first post-World War I season of 1919–20. The club then joined the Football League's new Third Division and finished 17th in their first season. In 1921, the Third Division was regionalised with Southend United joining the southern section and here they remained until the league re-structured in 1958. Southend came close to promotion twice when they finished 3rd in 1932 and 1950, the club's highest league positions until 1991.

### 1958–1981

Southend United joined the new national Third Division in 1958, where they remained until 1966 when they suffered their first relegation, into the Fourth Division. The club had to wait six seasons until 1972 to experience the club's first Football League promotion, as runners-up behind Grimsby Town. In 1976 Southend suffered relegation again before taking another runners-up spot behind Watford in 1978. Another relegation in 1980 was directly followed by one of the most successful seasons in the club's history as they won the Fourth Division Championship in 1981, breaking a series of club records in the process. Despite success on the pitch and low admission prices, the club's gates were low and condemned as "a bad reflection on the town".$^{:72}$

### 1981–1987

Many of Southend United's most gifted players were sold due to a financial strain.$^{:74}$ In June 1983 Anton Johnson, a local butcher who was also chairman of Rotherham United,$^{:74}$ bought 44.9% of the club from the Rubin brothers. The club was already £250,000 in debt.$^{:147}$ By August 1983 Dave Smith had been replaced as manager by Peter Morris who lasted until February 1984. On his arrival, Morris discovered that he had a squad of only ten players.$^{:121}$ Bobby Moore was installed as chief executive with Andrew MacHutcheon as chairman. The club were relegated into the Fourth Division in 1984 with Bobby Moore as manager. One of the club's darkest hours saw a season average attendance of barely above 2,000. Vic Jobson was elected as a director in the 1984 close-season, only to be forced out, along with MacHutcheon, months later.$^{:75}$ On the pitch, the team finished in 20th place, narrowly avoiding the need to seek re-election to the Football League.
Johnson was arrested on 23 October 1984. Two weeks before Christmas, fans discovered that £70,000 of the club's Christmas savings scheme had gone missing. While the fraud squad investigated, Robert Maxwell and Ken Bates stepped in, at Jobson's request, to lend the necessary money to the club to repay its Christmas savers. The club was now over £800,000 in debt.$^{:76}$ Johnson was banned by the FA from any future involvement in football, having simultaneously been in control of Southend, Rotherham and Bournemouth. Johnson was cleared of all charges at Chelmsford Crown Court and has never received the monies he personally invested in the misplaced Christmas fund and lost his shares in a further court case to the SUFC board. Over a decade later, Ceefax reported that Johnson was seeking to take over Doncaster Rovers.

### 1987–1992

Promotion in 1987 was the beginning of a golden era for Southend United. Relegation in 1989 was a mere blip as two successive promotions in 1990 and 1991 saw Southend United become "full members" of the Football League for the first time in the club's history, and in 1992 Southend United finished 12th in the old Second Division, their highest ever position in the Football League to date. On New Year's Day, 1992, the club briefly topped the Second Division but their dreary late season form stopped any hopes of a unique third successive promotion that would have given them a place as a Premier League founder member. Manager David Webb then stepped down.

### 1992–2003

Southend United were managed by Colin Murphy, Barry Fry and then Peter Taylor over the next three seasons. In 1995, former Liverpool player Ronnie Whelan agreed to become player-manager, and Southend finished 14th in Division One in his first season as a manager, a year later the club suffered relegation after finishing bottom of Division One. Ronnie Whelan left the club, claiming a lack of support from the fans and a lack of money from the chairman. Subsequently, Whelan won a case for wrongful dismissal.
Alvin Martin was named Whelan's replacement. Martin was unable to avoid a second consecutive relegation which Southend once again finishing bottom of the table and were duly relegated to Division Three. First team regulars Simon Royce, Jeroen Boere, Andy Thomson and Andy Rammell all left the club and were replaced by Martyn Margetson, Mark Beard, Mark Stimson and Rob Newman. Alvin Martin left in April 1999, with Southend fifth from bottom in the Football League.
Alan Little took charge of his first game away to Leyton Orient, a game Southend lost 3–0. Alan Little, who had previously managed York City, signed former York City players Mark Tinkler and Martin Curruthers. With limited success gates were barely getting above the 3,000 mark and a crowd of only 2,403 showed up to watch the game against Kidderminster and Alan Little's reign had come to an end.
David Webb left Yeovil Town and was appointed the new manager, signing players Darryl Flahavan, Leon Cort, Tes Bramble and Mark Rawle. During the season David Webb became ill and Rob Newman took temporary charge, being appointed permanently when Webb quit the club. Southend suffered straight defeats to Lincoln, Swansea, Kidderminster and Hartlepool, and Newman was dismissed shortly after. Steve Wignall took over as manager and signed Drewe Broughton, Mark Gower, Mark Warren and Che Wilson. He released goalkeeper Darryl Flahavan after he deemed him too small to play in the League, but re-signed him after a poor run of results. Two more defeats followed and Wignall was sacked. In late 2003 former Southend United midfielder Steve Tilson was appointed manager and named former Leyton Orient boss Paul Brush as his assistant.
During this period, Martin Dawn PLC and Delancey Estates, together forming South Eastern Leisure (SEL), had taken control of Southend United in November 1998, buying the club and its centrally located Roots Hall ground for £4m from then chairman Vic Jobson, who at the time owned 55% of the issued share capital of the club. Jobson had previously sold part of the ground's South Bank for housing, and SEL's plan was to continue the redevelopment and move the club to a proposed 16,000-seat stadium in a leisure redevelopment in the northern part of Southend.

### 2003–2005

Southend reached their first ever national cup final in 2004 when they met Blackpool in the final of the LDV Vans Trophy at the Millennium Stadium in Cardiff. Over 20,000 Southend fans travelled, but the team did not rise to the occasion and Blackpool won 2–0.
In 2004 Tilson and Brush were installed as a permanent management / coaching duo and led Southend to promotion to League One in 2005, while making a second successive appearance in the Football League Trophy final, which the Shrimpers lost 2–0 to Wrexham, but the third appearance at the Millennium Stadium in the League Two play-off final against Lincoln City brought success as Freddy Eastwood and Duncan Jupp scored the goals that gave the club their first ever taste of promotion via the play-off system and their first major piece of silverware since 1981.

### 2006–2009

On 29 April 2006, the Shrimpers were promoted to the Football League Championship after a 2–2 draw with Swansea City at the Welsh club's new Liberty Stadium. Southend were crowned League One champions on 6 May 2006 after beating Bristol City 1–0 at Roots Hall in front of over 11,000 fans. This was the last professional appearance of Shaun Goater; fans from his former club Manchester City came to give him a special send-off at the end of a long and distinguished career. For Southend United, the title was the club's first in 25 years. On 6 May 2006, Tilson was named as the League Manager Association's Manager-of-the-Season for League One.

#### 2006 League Cup win over Manchester United

Southend beat Leeds United in the third round of the League Cup and the draw for the fourth round set up a home tie against trophy holders and Premier League Champions Manchester United on 7 November 2006. The away side fielded a strong team, which included 10 players capped at international level. Cristiano Ronaldo and Wayne Rooney were amongst the starting line up, along with Gabriel Heinze, Darren Fletcher, Wes Brown and Alan Smith. Southend had injuries to strikers Billy Paynter and Lee Bradbury while Matt Harrold was cup tied so boss Steve Tilson partnered Gary Hooper up front with Freddy Eastwood. After 25 minutes Jamal Campbell-Ryce was fouled by David Jones 30 yards from goal; Kevin Maher, Steven Hammell and Freddy Eastwood stood over the free kick, then Eastwood curled "a wonderful free-kick around the wall and into the top corner past Tomasz Kuszczak" as the BBC reported. Southend held on for one of the most famous victories in the club's history. As this is the only meeting between the two sides to date, Southend are one of four sides with a 100% record against the Red Devils (along with Zenit St Petersburg, Vasco de Gama and Bootle Reserves - who defeated Newton Heath, the original name of Manchester United, in the 1890/91 FA Cup 2nd qualifying round).

#### Relegation to League One

Southend started the 2006–07 season reasonably well, beating Stoke City 1–0 on the opening day and a few games later Sunderland 3–1. Southend then did not win a league game for 18 games until 9 December 2006 when they beat Southampton 2–1 and West Bromwich Albion 3–1. On New Year's Day 2007, Southend picked up their first away victory of the season over Cardiff City, followed by a 3–1 victory away to Birmingham City on 31 January 2007 which lifted the Shrimpers from the bottom of the division on goal difference. On 9 February 2007, the Shrimpers defeated Queens Park Rangers 5–0 – a disastrous return for Southend's former goalkeeper Simon Royce. Southend escaped the relegation zone on 13 March 2007 when the Blues gained a 1–0 victory over Burnley. But after a 3–0 home defeat to rivals Colchester and only 10 league wins in the season, the Shrimpers were relegated back to League One.
On their return to League One Southend had bolstered their squad, adding Striker Charlie MacDonald, Winger Tommy Black and centre midfielder Nicky Bailey to their ranks. Despite the sale of Freddy Eastwood, Southend finished sixth in League One at the end of 2007–08 much to the thanks Lee Barnard, a January signing from Tottenham Hotspur, scoring 9 goals in 13 games, thus qualifying for a play-off place against Doncaster Rovers. Southend drew the home leg 0–0, but lost the second leg 5–1.
Following the play off defeat to Doncaster Rovers manager Steve Tilson began a mass summer clear out when Goalkeeper Steve Collis, Defender Lewis Hunt, Winger Tommy Black and club captain and loyal servant for over 10 years Kevin Maher were all released. Forwards Matt Harrold, Charlie MacDonald, Gary Hooper and Richie Foran were transfer listed. Darryl Flahavan and Mark Gower both turned down new contracts to sign for Championship sides Crystal Palace and Swansea City respectively. Simon Francis, Peter Clarke and Nicky Bailey were also later placed on the transfer list after failing to agree new contracts at the club. Francis later agreed and signed a new two-year deal. Bailey was being chased by Championship side Charlton Athletic, Bailey put in a man of the match display on Southend's opening game of the season against Peterborough United which was being watched by the London club, the game proved to be Bailey's last for Southend and he signed for Charlton three days later for £500,000 which could rise to £750,000. Peter Clarke remained on the transfer list for the entire season stating that he "never wanted to leave and never asked to be transfer listed" but wanted to concentrate on his football and discuss his future at the end of the season.
Southend pulled off the shock of the summer transfer market with the deadline day signing of Crystal Palace legend Dougie Freedman, the Scotsman signed a two-year contract at Roots Hall just minutes before the window shut. Manager Steve Tilson was delighted to bring Freedman to Roots Hall adding some much needed experience to Southend's forward line, something The Blues had been without since the retirement of Shaun Goater. Tilson also signed goalkeeper Steve Mildenhall from Yeovil Town as his new number one following the departure of Darryl Flahavan and the shot stopper became a firm favourite with the Southend fans. With Kevin Maher's departure Adam Barrett was officially named new club captain. Southend ended the season well with a run of just one defeat in nine games in February and March, that form was much down to two loan signings: Theo Robinson, a striker who signed until the end of the season from Championship side Watford, and France U21 centre back Dorian Dervite signed from Tottenham Hotspur also until the end of the season. Both were influential in Southend's late surge up the League One table. Despite this good form, Southend missed out on a play-off place with an eighth-place finish. Peter Clarke, who had remained on the transfer list for the entire season won the club's player of the season award before leaving the club and signed a three-year deal with League One rivals Huddersfield Town. Clarke admitted that he was leaving with a heavy heart, thanking the fans and management for their support.
The following day former manager David Webb was installed as Steve Tilson's new assistant. Webb stated that his role was only until the end of the 2009/10 season.

#### Relegation to League Two

A dismal run of just one win in 2010 left Southend deep in trouble at the wrong end of the table, relegation was confirmed on 24 April 2010 away to Oldham despite twice coming from behind to earn a 2–2 draw. With League Two having a salary cap, high earners at the club left. Player of the season Simon Francis and goalkeeper Steve Mildenhall were placed on the transfer list, Francis was given permission to speak to League One side Brentford but he failed to agree terms. Winger Damian Scannell turned down a new deal to sign a two-year deal with Dagenham & Redbridge. Club captain Adam Barrett and vice captain Alan McCormack both had their contracts terminated by mutual consent. McCormack made a short switch to London signing a two-year contract with Charlton Athletic. Barrett later joined Championship side Crystal Palace where he linked up with former Southend coach Dean Austin and former Southend striker Dougie Freedman, assistant manager at Selhurst Park.
On 4 July 2010 manager Steve Tilson was put on gardening leave, ending his seven-year stint as manager. Chairman Ron Martin stated that he didn't see the fight from the players or the manager.

### 2009–2010: HMRC and administration fears

In October 2009 Southend faced a winding up order from HM Revenue & Customs over an unpaid tax bill of £690,000. The club were also hit with a transfer embargo, this left Steve Tilson with just 12 fit professionals due to injuries and suspensions to his already threadbare squad. George Friend, who was on loan with Southend from Wolves before the embargo was in place, was unable to have his loan extended, despite an agreement between the two clubs for the left back to stay at Roots Hall.
On 27 October 2009, Southend avoided the prospect of a winding up order but the club could still have fallen into administration, acquiring an automatic 10 point deduction so every point on the field was vital. Southend beat Gillingham 1–0 on 30 October with Lee Barnard scoring the winning goal in the 3rd minute of injury time. Southend avoided going into administration on 9 November having paid the outstanding tax bill of £2.135 million on 6 November. The Guardian reported "A previous high court hearing was told that HMRC originally presented a winding-up petition for a tax bill of £690,000, but applied to have the club put into administration when the debt became larger." On 12 December 2009 the transfer embargo was lifted.
On 10 February 2010, Southend were back in court for another unpaid tax bill, this time £205,000. Southend chairman Ron Martin claimed that he was refusing to pay because the initial tax bill of £2.1 million was overpaid, the winding up petition was adjourned for 28 days. On 9 March 2010, Southend confirmed that the players had not yet been paid for and February and the PFA had to pay the players for January, the club were placed under another transfer embargo until they paid the money back. On 10 March 2010 Southend were given a 35-day extension to pay the unpaid bill or face administration.
On 14 April 2010, Southend were granted a final seven days to pay the outstanding bill. On 20 April 2010 the fee of £378,500 was paid.
On 2 August 2010, all cases against Southend United were dropped and an agreement was reached with HMRC. Southend's transfer embargo was lifted later that week.

### 2010–2019

On 5 July 2010 former Sheffield Wednesday and Plymouth Argyle manager, Paul Sturrock was announced as the new manager with Tommy Widdrington as his assistant. Sturrock's first signings for Southend were former Northampton Town left back Peter Gilbert and striker Barry Corr who was released by Exeter City. Both players had played under Sturrock previously. Southend being under a transfer embargo both players could only sign pre contract agreements.
A squad of 17 players were only registered in time to play on the eve of the new season as the club's transfer embargo was lifted. Sturrock led Southend to a respectable 13th-placed finish in his first season. The club mounted a more serious challenge the following season, spending 11 weeks at the top of League 2, owing to the goals and form of Ryan Hall, Kane Ferdinand and Liam Dickinson. A subsequent decline in form meant the team had to enter the play-offs after finishing the season in 4th place with 83 points, a total that in any other year in League 2, would have won the league. Southend lost the play off semi-final against Crewe Alexandra 3–2 on aggregate.
A transfer embargo at the start of the 2012–13 season meant that the club started its campaign with a depleted squad. The loan signing of Britt Assombalonga from Watford proved a success as the youngster scored 12 goals in 18 appearances. Blues went on a run of 14 games unbeaten which saw them reach 4th in the table. At the turn of the year Southend's form dramatically dropped, although the club reached its first ever Wembley cup final in the Football League Trophy. Paul Sturrock was sacked 2 weeks before the cup final but was controversially asked to manage the team for the final. Sturrock refused and watched the game from the stand. The Blues took a record 33,000 fans to the match, but lost 2–0 to Crewe Alexandra.
Phil Brown was brought in as Sturrock's successor but picked up just one win in his eight games in charge as Southend finished the season in 11th position, with only six league wins at Roots Hall all season, a worse home record than Barnet and Aldershot who were relegated.
Brown brought in former Darlington Manager Dave Penney as his assistant, whilst retaining Graham Coughlan as first team coach. Bob Shaw was also brought in as Head of Scouting and Recruitment. Brown's first summer signing was full back John White who had been released from neighbours Colchester United. He also signed former Hull City winger Will Atkinson who had left Bradford City. In 2015 Phil Brown led the team, after a thrilling play-off final against Wycombe Wanderers (7–6 on penalties), into League One. At the end of the 2016/2017 season the club missed the play-offs for the Championship by only one point.
On 22 October 2019, Sol Campbell was appointed manager of Southend. Campbell took charge for his first game — a 3–1 home defeat to Ipswich Town — on 25 October.

### 2020–present
#### Financial difficulties

Financial difficulties, including a winding-up petition heard on 22 January 2020, resulted in non-payment of players' and other employees' wages in December 2019, after which players consulted with the PFA. At this point (9 January 2020), Southend were 22nd in League One, 15 points from safety after winning only one of 24 league games. Club chairman Ron Martin paid £140,000 after seven senior Southend United players were not paid their December 2019 wages on time, and met with all players to reassure them it would not happen again. The winding-up petition was dismissed after debts were cleared.
On 18 January 2020, Southend won their first league game under Campbell with a 2–1 victory away at Accrington Stanley, also a first league win since 21 September 2019. However, financial constraints prevented the club signing any new players during the January 2020 transfer window. On 2 March, Martin confirmed Southend was under an EFL transfer embargo due to an unpaid tax bill, while February's wages to players were not paid on time, resulting in further PFA involvement. On 9 March, Southend was charged with misconduct by the EFL for failing to pay players on time, and for fielding an ineligible player against Lincoln City on 1 February (on 2 June, Southend received a suspended three-point penalty and were fined £7,500 for these offences). On 11 March, a further HMRC winding-up petition was adjourned to 29 April; it was then adjourned three more times, eventually to 28 October 2020.

#### Double relegation

On 2 April 2020, during the COVID-19 pandemic in the United Kingdom, Southend put "several staff and some players" on furlough (temporary leave) under the UK Government's emergency job retention scheme. The club's chairman said "It enables the club to best manage its finances during this time of limited income", but the move was criticised by the PFA who said the club had "consistently" let players down over wages. On 9 June, Football League clubs in Leagues One and Two agreed to end the 2019–20 season; Southend were relegated to League Two. The following day, the club announced it was putting the whole playing squad on furlough, but players refused to accept the move. On 30 June 2020, manager Campbell and three assistants left the club by mutual consent.
On 13 August 2020, Southend United appointed Mark Molesley, formerly manager of Weymouth, as their new manager on a three-year contract. On 28 October 2020, the club finally settled tax debts of £493,931 with HMRC; as a result, a winding-up petition was dismissed by the High Court. On 9 April 2021, Molesley was sacked having only won eight games out of 45; the club were 23rd, five points from safety with six games remaining. Phil Brown returned as manager but could not rescue the situation; Southend suffered a second successive relegation on 1 May 2021 with a game to spare despite a 2–1 victory at Barrow, dropping out of the Football League after 101 years. Brown subsequently agreed a two-year contract to manage the club.
In April 2021, former Southend player Stan Collymore wrote to Martin offering to buy the club from him, and held talks concerning the potential appointment of a Collymore associate as the club's CEO. In May 2021, Tom Lawrence (formerly CEO at Gillingham) was appointed. In August 2021, Southend revealed their overall debt in July 2019 was £17.4M, having grown by £2.4M; Martin said the majority of the debt was owed to his companies, and that £6.8M of debt had already been written off. On 21 August 2021, Southend started their first season in the National League with a 1–0 victory at King's Lynn Town, but a six-match winless streak led Phil Brown to describe Southend as stuck in a massive "chasm". On 5 and 9 October 2021, Southend fans staged protests demanding the departure of chairman Ron Martin; following a 4–0 defeat by Chesterfield at Roots Hall on 9 October, Brown was sacked. Collymore offered further free support to the club, described by the BBC as "a mess" and "already on life support". Defender Jason Demetriou took temporary charge before, on 20 October 2021, Kevin Maher returned to the club as head coach. CEO Tom Lawrence also started negotiations with Collymore about a formal role with the club, and he was appointed the club's senior football strategist in early November 2021. In December 2021, Southend was placed under a National League embargo because of HMRC debts caused by the COVID-19 pandemic; after back-to-back relegations and 18 months of reduced income, CEO Lawrence said the club was "in a deteriorating income position". In May 2022, Southend finished their first National League season in 13th position.

#### Further financial difficulties

On 30 September 2022, the club was placed under a transfer embargo after a missed HMRC payment. Martin said the club's Time To Pay Agreement with HMRC had been cancelled prematurely, adding bridging finance would enable the club to discharge its HMRC debt in full. Nonetheless, in October 2022, HMRC issued a winding-up petition. Due to be heard at the High Court on 9 November, it was adjourned to 18 January 2023; the transfer embargo remained in place. After members of staff were late receiving their October 2022 salaries, the Shrimpers Trust and shirt sponsor PG Site Services each loaned the club £40,000, a gesture described by CEO Tom Lawrence as "humbling". November and some December 2022 wages for players and non-playing staff were also paid late. Lawrence said the club had a funding gap of about £2M a year; promotion to League Two would reduce current losses to more manageable levels; the club was then 6th in the National League.
With the club's final accounts for the year to 31 July 2020 still not filed (overdue since April 2021), on 3 January 2023, Companies House issued a first Gazette notice to have the company struck off. On 18 January 2023, the HMRC winding-up hearing was adjourned again, until 1 March 2023. In a 25 January 2023 statement, Martin could not "outline precise timings" regarding the bridging finance; he was later reported to be seeking a £5M loan to pay debts including £1.4M in unpaid tax owed to HMRC. The Shrimpers Trust did not expect the club to make a loan repayment due at the start of February, and, with players and other staff unpaid for January, anxious fans started planning a 'phoenix club' and there were unsuccessful attempts to engage with Martin over a possible sale of the club.
On 10 February 2023, St John Ambulance stopped providing first aid staff at Southend home games because of outstanding fees, forcing the club to find alternative medical cover ahead of an FA Trophy tie with York City. The following day, Martin said finding the money to clear the club's HMRC debt by 1 March "will be close". He said the debt was a legacy of unpaid PAYE for players' wages when Southend was in Leagues One and Two. Players' January wages remained unpaid ahead of Southend's 25 February game at Torquay United, and were eventually paid 28 days late; other staff had not been paid since November. Less than 24 hours before the winding-up hearing, the club said it had paid the £1.4M tax bill, adding that "funds as working capital" had also been injected into the club. At a brief hearing at the Insolvency and Companies Court on 1 March 2023, the winding-up petition was dismissed after HMRC confirmed payment of the debt. However, the transfer embargo remained in place; sponsors, angry at being kept in the dark, talked of taking legal action against the club; and supporters groups, fearing "the next crisis could be just around the corner", highlighted the "owner's inadequacies" and said a new beginning would only be possible "when a new structure and ownership is in place at the club".
On 30 April 2023, the club finished their second National League season in 8th position, outside the promotion and play-off places; non-playing staff at the club had not been paid for the past two months.

#### Club put up for sale

On 17 March 2023, the club commenced a formal process to explore the sale of the club or to bring in new investment partners.
Despite the February 2023 funds injection, the club's financial difficulties continued. On 6 April 2023, the club had paid all staff salaries up to March 2023, but some club office staff had yet to receive their March pay. On 14 April 2023, shirt sponsor PG Site Services said it would stop sponsoring the club "due to a breakdown of our relationship with the current owner RM and his conduct". Further doubt over Southend United's ongoing financial viability emerged on 4 May 2023 when the club was served another HMRC winding-up petition—their 18th—due to be heard in the High Court on 17 May. Three companies, including PG Site Services and Engie Power, were also involved in the petition regarding a £275,000 debt, but the hearing was adjourned to 12 July 2023, giving Martin more time to sell the club.
On 24 May 2023, Martin was said to be in advanced discussions with a group including Kimura Capital regarding purchase of the club. It was later reported that negotiations were taking place with "three interested parties", though none had been granted a period of exclusivity.
On 31 May 2023, the club secured a court order unfreezing a bank account to enable it to pay players (keeping them at the club) and accountants, but some club staff were still awaiting March or April wages in early June. Players and backroom staff again went unpaid at the end of June, and players refused to resume pre-season training until they were paid. Backing the players' decision to suspend training, the Shrimpers Trust offered to support unpaid club staff. On 5 July, another club sponsor, Midex PRO, withdrew its support due to "the current situation with the club's owners". While players were eventually paid, manager Maher and other backroom staff remained unpaid three days before the winding-up hearing, while club sale discussions were reportedly being held up by the stadium side of the transaction. A lack of medical cover meant players could not resume training on club premises. On 10 July, Martin told protesting fans the sale would not be completed before the winding-up hearing. On 11 July, the water supply to the club's training facility was turned off due to unpaid bills.
On 12 July 2023, the winding-up hearing was adjourned for a second time, to 23 August 2023, to allow further time for a sale to be concluded, amid doubts about the club's ability to meet National League requirements, with football finance expert Kieran Maguire describing Southend as "one of the worst run clubs in the country". On 14 July 2023, a pre-season friendly against Billericay Town was cancelled 24 hours before its scheduled kick-off. Southend reportedly had just 14 contracted players and blamed "injuries to contracted players" for the postponement. Local MPs Anna Firth and Sir James Duddridge also became involved, with Firth pressing Martin to provide the National League with a full list of football creditors, confirmation that all players and staff had been paid and a full safety certificate for Roots Hall. On 17 July 2023, Martin said he would sell his stake in the club for £1, but wanted £4.5M for Roots Hall. The club also needed £1M "in the short term" to settle its latest HMRC winding-up petition and lift a transfer embargo. On 20 July, Kimura Capital stated that they were no longer interested in leading a bid for the club but were involved in other discussions to save the club. However, in late July 2023, Martin told protesting fans—who he blamed for deterring potential bidders—that nobody had yet made him an offer on his terms.
On 21 July 2023, the club was given court permission to pay £300,000 in football-related debts to remain in the National League. Martin promised to notify other creditors, which include HMRC—owed £275,000—and energy supplier Npower, of the payment. This had to be approved by the court as the club was insolvent. Club staff were paid wages dating back up to three months on 26 July 2023, and were finally up to date with their wages, and July's wages were paid on time. The National League welcomed the club's payments to football creditors, licencing the club to participate in the 2023–2024 season, but required it to pay its HMRC debt in full by 23 August 2023 (adjournment of the court hearing would not postpone this requirement) and to ensure all future football creditors or HMRC debts were cleared on time during the 2023–2024 season. A breach of these conditions would result in an immediate and automatic 10 points deduction.
To ready Roots Hall for the new season, the club cancelled another pre-season friendly, against AFC Wimbledon on 29 July. On Sunday 30 July, over 160 fans volunteered to clean and paint the stadium to help it gain a new safety certificate. With a matchday squad of just 15 players due to the club's transfer embargo, Southend won their opening two games of the season, beating Oldham Athletic and Dagenham & Redbridge, but lost the next two. The future of the club's academy was also in doubt as it was no longer eligible for EFL funding.
On 15 August 2023, former club chief executive Tara Brady confirmed he had tried to buy Southend United in July, only to be rebuffed by Ron Martin. Jez Moxey, of the club's selling agent General Sports Worldwide, said talks to sell the club were continuing "with interested parties who have signed NDAs, shown proof of funds and demonstrated a seriousness about acquiring control of Southend United FC".

#### Points deduction

On 23 August 2023, the winding-up hearing was adjourned for a third and final time, to 4 October 2023, with Judge Sebastian Prentis telling Martin if he was in charge of any other business it would have been wound up. As part of the £275,000 HMRC debt remained outstanding (in addition, Npower was owed a similar amount and electrical contractor Emersons was owed £600,000), the club were deducted 10 points by the National League (it appealed against the penalty, unsuccessfully). Martin told the court he was "confident" a sale to an Australian buyer—later named as Justin Rees—should be finalised by the end of September. The judge said the club would be wound up if the deadline was missed. Despite his earlier confidence, Martin subsequently said he was unsure if this deadline would be met; there were two potential buyers though discussions with the Rees consortium were "more advanced".
On 7 September 2023, Southend Council committed to considering investment in the club if it would aid its survival, potentially by buying Roots Hall for Martin's £4.5M asking price. It later emerged that the proposal might be financially supported by the Department for Levelling Up, Housing and Communities which had invited applications for grants of up to £2M from its community ownership fund. The Shrimpers Trust Board expressed interest to the fund in bringing "ownership of the freehold of Roots Hall Stadium and its facilities into the hands of those who value it most – our local community of Southend-on-Sea". The deadline for bids is 11 October 2023.
On 16 September 2023, Southend lost 3–0 at York City and had two players sent off. The resulting suspensions, plus injuries to other players, left the club with just 10 available players ahead of a match against Maidenhead United on 19 September, with manager Kevin Maher appealing against the red cards and talking to the National League about bolstering his squad. The club signed former West Ham goalkeeper David Martin to make his immediate debut, with Portuguese midfielder Mauro Vilhete one of just two substitutes, as Southend won 2–0.
Meanwhile, also on 19 September, the club was due to appear at Basildon magistrates' court in a civil matter relating to a disputed electricity bill from Npower Business Services (part of E.ON); consideration of the 'application for warrant of entry' was postponed to Chelmsford magistrates' court on 3 October 2023 when it was adjourned to an unspecified future date.
On 20 September 2023, the Justin Rees consortium said it had made two bids to Ron Martin, but neither had been accepted, and it was "unlikely that any deal can be agreed prior to the 4th of October court appearance date". The consortium understood Martin would ensure the club avoided liquidation on 4 October, but administration remained a risk. Few details of the consortium's bid were released, but—due to "the non-viability of a new stadium at Fossetts Farm"—it involved retaining and upgrading Roots Hall as the club's stadium, taking ownership of the stadium and the club's training ground, and Martin contributing funds towards Roots Hall's redevelopment. On 29 September 2023, local councillors were optimistic that a deal could be agreed before the High Court hearing; rumours of a deal grew on 2 and 3 October 2023.
Meanwhile, fans staged an anti-Martin protest march to Roots Hall ahead of the club's National League tie against AFC Fylde on 23 September 2023. Southend fielded a 14-man squad, and lost the game 2–1. Two draws, at Aldershot Town three days later and at Rochdale on 30 September, left Southend in 23rd place, three points from safety.

#### Proposed club sale to Justin Rees consortium

On 3 October 2023, the club confirmed that they had reached an agreement for the sale of the club to the Justin Rees consortium, with a formal takeover and completion date of 1 November, later revised to 17 November 2023 and then the end of the month. The club would remain at Roots Hall, with the 500 homes once planned for the site now transferred to Fossetts Farm (a move agreed by Southend's council in early November). The deal was announced the day before the High Court hearing of HMRC's winding-up petition, amid reports that the HMRC debt had now been paid, and the winding-up petition was duly dismissed.
On 4 December 2023, with the takeover still not completed, a Southend United supporters group said it would stage a protest unless an update on the club's sale was provided. On 5 December, the consortium said due diligence had raised important issues which had required further time to resolve, and some legal and procedural work remained. The exact completion date would be confirmed "once it is locked in", and the consortium would work with HMRC and the National League to arrange for the simultaneous lifting of the transfer embargo.
On 23 December 2023, Martin and the Rees consortium exchanged contracts for the sale of the club; the deal remained conditional upon Southend Council's approval of certain property transactions and the club ownership was expected to be formally transferred in February 2024. However, on 8 March 2024, Southend CEO Tom Lawrence said final completion of the club's takeover could still be a couple of months away, being dependent upon a council review of the housing shift to Fossets Farm, though it later emerged that obtaining the consent of Ron and son Jack Martin's finance partner (CBRE) was also delaying matters. As a result, one impatient creditor (Stewarts Law) petitioned for the club to be wound up (the club's 19th such petition); the High Court hearing was subsequently adjourned. On 6 April, Ron Martin said he expected to have sold the club by mid-May 2024.
On the pitch, the delayed takeover and ongoing National League sanctions meant that Southend had just one substitute for their league game against Bromley on 16 December 2023; after an injury to goalkeeper David Martin, right-back Gus Scott-Morriss finished the game in goal. Local MP Anna Firth cited this incident in a letter to the National League about its sanctions' "disproportionate" impacts on the club. After 15 months, Southend's transfer embargo was lifted on 28 December 2023. Southend finished the 2023–24 National League season in 9th place. Without the 10-point deduction they would have finished sixth.
By 8 May 2024, it was clear the sale would not be completed by mid-May; the council's due diligence over plans for the housing at Fossetts Farm continued, while CBRE had yet to consent to the payment structure for the Roots Hall refurbishment. At the club's winding-up petition hearing on 15 May, the consortium and Martin sought a six-week adjournment, supported by Stewarts Law and two other creditors. The club was given six weeks to settle with creditors or face liquidation. As a consequence of the unresolved winding-up order, Southend was placed under a fresh transfer embargo on 17 May 2024.
On 23 May 2024, after a Council update and having provided £3.5m in funding to Southend, the Rees consortium said it was "increasingly concerned" that processes would not be completed. On 7 June 2024, the consortium ("Custodians of Southend United", COSU) said Southend United could go out of business as a property element of the contract might not be signed ahead of the 26 June winding-up hearing date. Southend Council and the Martins were in renewed negotiations about the deal. The newly elected council leader Daniel Cowan blamed the previous administration for assurances that "fell outside of normal practice and were simply not achievable"; the Fossetts Farm housing developer (Citizen Housing) was said to be modelling a new proposal that would help safeguard the council from judicial review. On 14 June 2024, Cowan confirmed the proposed development had failed the council's due diligence process. Citizen Housing and the Martin family were given until 21 June 2024 to respond to new council proposals, with future council involvement dependent on COSU acquiring the club ("if COSU walk, so will we and we will not return"). While Citizen Housing had not met the council's 21 June deadline, there was sufficient progress to persuade Cowan to continue negotiations about new heads of terms ready for new due diligence. Nonetheless, the Shrimpers Trust said they might start a phoenix club and make Roots Hall an asset of community value if needed. Adding to the pressure, on 24 June 2024, the National League ordered Southend United to provide a £1m bond due to the ongoing uncertainty about their financial situation. The bond would remain in place until the COSU takeover was successfully concluded or the club could demonstrate it had sufficient resources to meet its financial obligations for the forthcoming season. COSU criticised the move, saying the National League was "only making the situation more difficult to resolve".
The day before the winding-up hearing, Stewarts Law reached a settlement with Southend United. On 26 June 2024, a payment plan was agreed with a second creditor (PG Site Services, owed £350,000) and the winding-up petition was dismissed in the High Court. On 2 July 2024, COSU was reported to have agreed terms with Ron Martin; the takeover was likely to be agreed first, ahead of negotiations and due diligence about the housing plans. On 19 July 2024, the COSU consortium completed its takeover of Southend United. Justin Rees became the new chairman, with day-to-day affairs managed by CEO Tom Lawrence. The Fossetts Farm development remained subject to due diligence by the city council.