History of the Edmonton Oilers Founded in 1971 , the Edmonton Oilers are a professional ice hockey National Hockey League ( NHL ) team based in Edmonton , Alberta . The team played its first season in 1972 – 73 as one of twelve founding franchises of the major professional World Hockey Association ( WHA ) . They were originally supposed to be one of two WHA teams in Alberta ( the other one being the Calgary Broncos ) . However , when the Broncos folded before the WHA ' s first season began the Oilers were renamed the Alberta Oilers . They returned to using the Edmonton Oilers name for the 1973 – 74 season , and have been called that ever since . The Oilers subsequently joined the NHL in 1979 ; one of four franchises introduced through the NHL merger with the WHA . After joining the NHL , the Oilers went on to win the Stanley Cup on five occasions : 1984 , 1985 , 1987 , 1988 and 1990 . For their success in the 1980s , the Oilers team of this era has been honoured with " dynasty " status by the Hockey Hall of Fame . WHA years ( 1972 – 79 ) . On November 1 , 1971 , the Edmonton Oilers became one of the 12 founding World Hockey Association franchises . The original team owner was Bill Hunter . Hunter owned the Edmonton Oil Kings , a junior hockey franchise . He also founded the Canadian Major Junior Hockey League ( now known as the Western Hockey League ) . However , Hunter ' s efforts to bring major professional hockey to Edmonton via an expansion NHL franchise had been rebuffed by the NHL . Therefore , Hunter looked to the upstart WHA instead . It was Hunter who chose the " Oilers " name for the new WHA franchise . This was a name that had previously been used as a nickname for the Edmonton Oil Kings in the 1950s and 1960s . After the newly founded Calgary Broncos folded prior to commencement of the inaugural WHA season , the Oilers were renamed the Alberta Oilers as it was planned to split their home games between Edmonton and Calgary . Possibly for financial reasons or to allow for a less complicated return of the WHA to Calgary , though , the team ultimately played all of its home games in the Edmonton Gardens and subsequently changed its name back to the Edmonton Oilers the following year . They won the first game in WHA history 7 - 4 over the Ottawa Nationals . The Oilers drew fans with players such as defenceman and team captain Al Hamilton , goaltender Dave Dryden , and forwards Blair MacDonald and Bill Flett . However , a relatively little - noticed move in 1976 would have an important impact on the history of the franchise . That year , journeyman forward Glen Sather was acquired by the Oilers . It turned out to be his final season as a player . However , he was named player - coach late in the season , moving to the bench full - time after the season . Sather would be the coach or general manager of the Oilers for the next 23 years . The team ' s performance would improve in 1978 , when new owner Peter Pocklington acquired Wayne Gretzky as an under - age player ( consequentially , his first year of WHA experience prevented him from being an official 1979 – 80 NHL rookie ) , as well as goaltender Eddie Mio and forward Peter Driscoll , from the recently - folded Indianapolis Racers for cash . Gretzky ' s first and only WHA season , 1978 – 79 , saw the Oilers finish first in the WHA standings , posting a league - best 48 – 30 – 2 record . However , Edmonton failed to win the championship , as they fell to the Winnipeg Jets in the Avco World Trophy Final . Dave Semenko of the Oilers scored the last goal in WHA history late in the third period of the final game , which the Oilers lost 7 - 3 . The Oilers joined the National Hockey League for 1979 – 80 , along with fellow WHA teams Hartford Whalers , Quebec Nordiques , and the Jets following a merger agreement between the two leagues . Of these four teams , only Edmonton has avoided relocation and renaming ; the Nordiques became the Colorado Avalanche in 1995 , the Jets became the Phoenix Coyotes in 1996 , and the Whalers became the Carolina Hurricanes in 1997 . Entry into the NHL ( 1979 – 1983 ) . The Oilers lost most of the players from 1978 – 79 when the NHL held a reclamation draft of players who had bolted to the upstart league . They were allowed to protect two goaltenders and two skill players . Originally , Gretzky was not eligible to be protected ; under the rules of the time , he normally would have been placed in the Entry Draft pool . However , Pocklington had signed him to a twenty - one year contract in 1979 . Pocklington used the contract to force the NHL to admit the Oilers : he promised the league that Gretzky would fill every arena , but that since he was under a personal services contract to Pocklington , the only way Gretzky would enter the NHL was as an Oiler . The league relented , allowing the Oilers to protect Gretzky . In the expansion draft , Sather and general manager Larry Gordon carefully restocked the roster . Sather later said that out of 761 players on the draft list , only 53 really interested him . He concentrated on drafting free agents , since the Oilers would get compensation if they signed somewhere else . He estimated that this saved the Oilers as much as $ 500 , 000 that could be used in the Entry Draft . The Oilers were mediocre during the regular season in their first two seasons , finishing sixteenth and fourteenth respectively . However , due to the fact that 16 of the 21 NHL teams made the playoffs at the time , the Oilers were still able to get their young players experience in the playoffs ( they would make the playoffs for ther first thirteen years in the NHL ) . They won only one playoff series over this time span though , upsetting the Montreal Canadiens in 1980 - 81 . Also , they still had great draft positions . This allowed the Oilers to put together a young , talented , experienced team quickly . Within three years , Sather and chief scout Barry Fraser had drafted several players who would have an important role in the team ' s success , including Mark Messier , Glenn Anderson , Jari Kurri , Paul Coffey , Kevin Lowe , Grant Fuhr and Andy Moog . However , the Oilers improved over the next two seasons , finishing second and third respectively . They failed to capitalize on their success in 1981 - 82 , as they were upset by the Los Angeles Kings in five games ( game three of this series , now known as the Miracle on Manchester , saw the Oilers take a 5 - 0 lead , only to lose 6 - 5 to the Kings in overtime ) . Next year , though , the Oilers advanced all the way to the Stanley Cup Finals ( losing only once in the process ) before getting swept by the New York Islanders . During this season , Gretzky , Messier , Anderson , and Kurri all topped the 100 point plateau , with Coffey not far behind at 96 . After the season , Lee Fogolin resigned as captain of the Oilers , picking Gretzky as his successor . During this period , Wayne Gretzky began setting new NHL records . In his first season , he was ruled ineligible for the Calder Memorial Trophy ( rookie of the year ) ( because of his previous NHL experience ) and the Art Ross Trophy ( NHL scoring leader ) ( although Gretzky tied with Marcel Dionne of the Los Angeles Kings in points , Dionne won the trophy on the basis of scoring two more goals ) . However , Gretzky still managed to win his first of an NHL record eight consecutive and nine total Hart Trophies . Next season , Gretzky quickly made up for not winning the Art Ross Trophy by winning his first of an NHL record seven straight and ten total . He easily won the Art Ross by setting new single season records for assists ( with 109 ) and points ( with 164 ) . In 1981 - 82 , Gretzky set the single season record for goals with ninety - two . Also , he became the first player in NHL history to score 200 points ( with 212 ) . After the season , he won his first of a record four consecutive and five total Lester B . Pearson Awards ( NHL MVP as selected by NHL players ) . Gretzky wasn ' t the only player to set a record during this time ; Grant Fuhr set an NHL goaltender rookie record in 1981 - 82 by going undefeated in twenty - three straight games . Also , the Oilers became the first NHL team to score four hundred goals in a season , a feat they would accomplish for five straight years . Dynasty years ( 1983 – 1990 ) . In 1983 – 84 , the Oilers finished first overall in the NHL , winning a franchise record fifty - seven games and earning 119 points ( fifteen points ahead of the second place Islanders ) . They scored 446 total goals , a record that still stands . In addition , the Oilers scored a league record 446 goals , a record that still stands . Gretzky broke the 200 point barrier for the second time in his career ; the Oilers also became the first team in NHL history to have 3 players score more than 50 goals : Gretzky ( 87 ) , Kurri ( 54 ) , and Anderson ( 52 ) . Finally , Paul Coffey became the second defenceman in NHL history to score 40 goals in one season . He finished with 126 points . In the Smythe Division semifinals , the Oilers swept the Winnipeg Jets . In the division finals , the Oilers faced a tougher challenge from the Calgary Flames , but ultimately prevailed in Game 7 , disposing of their provincial rivals 7 - 4 after trailing 4 - 3 midway through the second period . After sweeping the Minnesota North Stars in the conference finals , the Oilers earned a rematch with the Islanders in the Stanley Cup Finals . The Oilers split the first two games in Long Island , but then won three in a row in Edmonton to become the first former WHA team to win the Stanley Cup . After the series , Mark Messier was awarded the Conn Smythe Trophy as playoff MVP . Eight Oilers were selected to compete for Canada at the 1984 Canada Cup . As a result , the Oilers were not as overwhelming in the 1984 - 85 season as they had been in the previous year . The team did not push as hard in the regular season , trying to stay as fresh as possible , and Sather even took a week ' s vacation to Hawaii in the middle of the season . . Still , the Oilers finished second overall in the NHL with 49 wins and 109 points , four behind the Philadelphia Flyers . Gretzky scored the 1 , 000th point of his career in only his 424th game en route to a league - leading 73 goal , 208 point season . Kurri also topped the 70 goal plateau , finishing with 71 goals and 135 points . Paul Coffey had his second straight 120 point season , finishing with 37 goals and 121 points . In the playoffs , the Oilers swept the Kings in 3 games in the opening round , and the Jets in the division finals . The team met Chicago in the Campbell Conference Finals , jumping out to a 2 - 0 series lead and extending their playoff win streak to 9 games . Chicago , stressing physical and agitating play to slow the Oilers ' attack , tied the series on home ice before the Oilers won the last two games to finish the series in six . The Oilers scored 44 goals against the Black Hawks , an NHL record for one team in a single playoff series that still stands . Edmonton repeated as Stanley Cup champions in 1985 , overpowering Philadelphia in five games . Kurri tied Reggie Leach ' s record for goals in one playoff year with 19 . Coffey set a new record for playoff points in a season by a defenceman with 37 , but it was Gretzky with the highest numbers of all , scoring a playoff record 47 points and registering a staggering + 28 in only 18 playoff games . For his efforts Gretzky was awarded the Conn Smythe Trophy , but Coffey and Fuhr were also considered strong candidates . Jari Kurri won the Lady Byng Trophy , and Paul Coffey captured the first Norris Trophy of his career . Gretzky , Kurri and Coffey were all named to the NHL ' s First All - Star Team . The Oilers were indeed a juggernaut that the entire NHL feared , but the off - ice antics of some players began tarnishing the team ' s image by the time the 1985 - 86 season got underway . In June 1985 , Dave Hunter was charged with impaired driving . He was later convicted in February 1986 and sentenced to one week in jail , which he served in the middle of the season . Then on September 6 , 1985 , Mark Messier lost control of his Porsche and totalled it by hitting three parked cars . He was later charged with hit and run and careless driving , for which he paid a fine . . In addition , the Oilers acquired Craig MacTavish , a talented defensive centre from Boston , who had just served a year in jail for vehicular homicide . In spite of the distractions the Oilers were again the top team in the NHL during the regular season , with 56 wins and 119 points . They won the inaugural Presidents ' Trophy , the trophy given to the team with the best regular - season record . Gretzky set a new league record for points with 215 , and amassed a new league record 163 assists . ( At that time , no player had scored that many points in a season . The only player who has done it since is Mario Lemieux . ) Jari Kurri led the NHL in goals with 68 , finishing with 131 points , and Paul Coffey set a new record for goals by a defenceman with 48 . He finished with 138 points , one point behind the all - time record for defencemen set by Bobby Orr . Additionally , the Oilers matched a record they set in 1983 - 84 with 3 players who scored more than 50 goals : Kurri ( 68 ) , Glenn Anderson ( 54 ) , and Gretzky ( 52 ) . The Oilers overpowered Vancouver in the divisional semi - finals , sweeping the series 3 - 0 and outscoring the Canucks 17 - 5 . The Oilers faced their most bitter rival in the division finals , the Calgary Flames . In a physical and sometimes dirty series , in which Flames ' enforcer Nick Fotiu actually tried to climb into the Oilers ' bench to get at Glen Sather , the Oilers and Flames fought a classic series through the first 6 games , with the deciding game to be played April 30 , 1986 at Northlands Coliseum . Shockingly , the Oilers ' bid for a third straight championship — " three - peat " — came to an end . In the third period of a 2 – 2 tie , on his 23rd birthday , rookie defenceman Steve Smith banked his breakout pass off goaltender Grant Fuhr ' s left skate and into the Oilers ' net . Despite a late flurry the Oilers were unable to tie the score , and the own goal stood as the game - and - series - winning goal . After the season , the Oilers ' players again won several awards : Wayne Gretzky won his seventh straight Hart Trophy , along with his sixth straight scoring title . Paul Coffey won his second consecutive Norris Trophy , and Glen Sather took home the Jack Adams Award as the NHL ' s Coach of the Year . Gretzky and Coffey were named to the First All - Star Team , and Kurri was named to the Second All - Star Team . In the May 12 , 1986 issue of Sports Illustrated , an article was published alleging more problems with the off - ice activities of the Oilers . The article , written by Armen Keteyian and Donald Ramsay , suggested that five team members had " substantial " cocaine problems . Citing sources from around the league and from the RCMP ' s Edmonton Drug Unit , alleges rampant drug use within the team , a high - pressure citywide environment that put immense pressure on players , and a culture of ensuring the players ' drinking problems remained under wraps . The financial problems of certain players were also brought up , most notably those of Grant Fuhr . The Hockey News ran a responding article in which Sather called the allegations innuendo . NHL President John Ziegler and NHLPA President Alan Eagleson dismissed the story as McCarthyism . . Sports Illustrated stood by its story ; suddenly , the Oilers ' organization had an image problem to fight . After already being tarnished by the Messier and Hunter episodes in the last year , they were now widely suspected of rampant drug use . It was at this point that Edmontonians became noticeably less enthused with the Oilers , and in spite of having one of the most powerful teams in NHL history , interest in the team began to decline . The 1986 – 87 season saw the Oilers come together as a team , determined to recapture the Stanley Cup . Except for a poor record against the Flames , Edmonton again dominated the regular season , finishing first overall with 50 wins and 106 points , six points ahead of second - place Philadelphia . The team captured its second consecutive Presidents ' Trophy , and last to date . Wayne Gretzky ( 62 goals and 183 points ) and Jari Kurri ( 54 goals and 108 points ) finished first and second in the NHL scoring race . Mark Messier ( 37 goals and 107 points ) finished fourth . Paul Coffey missed 21 games with injuries but still managed 67 points . The season was notable for the deteriorating relationship between Coffey and Head Coach Glen Sather . The relationship was laced with antagonism for most of the season , and Coffey believed he was the victim of a double - standard in treatment of the players . At the 1987 NHL trade deadline , the Oilers acquired Kent Nilsson for a second round draft pick in 1988 , which solidified Edmonton ' s top two lines in time for the playoffs . In the opening round of the playoffs , the Oilers lost their first game to Los Angeles before winning the next four straight . Game Two saw the Oilers establish a new NHL record for playoff goals in a single game with 13 . The Oilers faced the Winnipeg Jets in the Smythe Division Finals , and Grant Fuhr was the big star in what became an Edmonton sweep . In the conference finals against the Detroit Red Wings , the Oilers again lost the first game on home ice before rebounding to win the next four . Edmonton returned to the Stanley Cup Final and faced the same opponent as they had in 1985 , the Philadelphia Flyers . Though the Oilers dominated the territorial play and shot counts in the series , the goaltending of Flyers ' rookie Ron Hextall brought the Flyers back from a 3 - 1 series deficit and set up a decisive Game Seven at Northlands Coliseum . In the seventh game the Oilers fired 43 shots at Hextall : Oiler stars Messier , Kurri , and Anderson were able to solve Hextall for a goal apiece , and for perhaps the first time in franchise history , the Oilers clamped down on defence ; the more mature Edmonton squad held the Flyers to just two shots in the third period , and a total of 20 in the game , en route to a convincing 3 – 1 victory . In the post - game celebration , Gretzky immediately passed the Stanley Cup to Steve Smith , now vindicated after his costly miscue the previous season . Gretzky led the playoffs in scoring with 34 points and Kurri led in goals with 15 . However , the Conn Smythe Trophy was awarded to the Flyers ' Hextall : it was only the second time in NHL history that the Conn Smythe Trophy was awarded to a player on the losing side . The Oilers again collected several awards after the season . Gretzky claimed his eighth Hart Trophy as most valuable player in only his eighth year in the NHL , along with his seventh straight Art Ross Trophy . Gretzky also captured the 5th and final Lester B . Pearson award of his career , along with his third career Plus - Minus Award . Gretzky and Kurri were named to the NHL ' s First All - Star Team . Seven Oilers ( five for Canada , two for Finland ) took part in the 1987 Canada Cup . When training camps for the 1987 – 88 season opened , several Oilers ' players were MIA . Mark Messier missed all of training camp while his contract was renegotiated . Glenn Anderson failed to report until the season started , and Paul Coffey did not report at all , unhappy with both his contract and his treatment by the club . Mike Krushelnyski was unhappy with his ice - time and skipped training camp . Kent Nilsson and Reijo Ruotsalainen both decided to play the season in Europe . Andy Moog also refused to report : he no longer wanted to play backup to Grant Fuhr and instead joined the Canadian Olympic Team . He was later joined by Randy Gregg . Eventually , Sather dealt away the first of his great players . Paul Coffey was the centrepiece of a multi - player deal with the Pittsburgh Penguins . Among the players Edmonton received in return was young left - winger Craig Simpson , who was brought in to play alongside Messier and Anderson . Simpson finished the season with 56 goals , the second - highest total in the league . Eventually , Andy Moog was dealt to Boston for speedy winger Geoff Courtnall and promising young goalie Bill Ranford . Without Coffey ' s offence on the point , and missing Gretzky for 16 games during the season with injury , and perhaps continuing the Canada Cup trend from 1985 , the Oilers ' regular season was not an impressive one by their standards . Wayne Gretzky lost the scoring title outright for the first time in his career , finishing with 149 points to Mario Lemieux ' s 168 . ( Gretzky ' s points - per - game average was still higher than Lemieux ' s , however . ) In addition , the Oilers ' drive for a seventh consecutive Smythe Division title was stymied , and they were dethroned by their provincial rivals , the Flames , who also won the Presidents ' Trophy . The Oilers finished the season with 44 wins and 99 points , good for 3rd place overall in the NHL . For the first time in six years , the Oilers did not score the most goals in the league . They amassed 363 goals , second to the Flames ' 397 . One bright spot on the team , however , was the play of Grant Fuhr . He started a league - record 75 games , posting a team - record 40 wins . Mark Messier placed seventh in the league scoring race with 37 goals and 111 points . In the first round of the playoffs , the Oilers dispatched of the third place Winnipeg Jets in five games . Next up was a looming showdown with Calgary , and hockey experts almost unanimously predicted a Flames ' victory . However , the series became an Edmonton sweep , with Gretzky notching his second career playoff overtime winner in Game Two . In the Campbell Conference Finals against Detroit , the Oilers again prevailed in five games , matching their total from the previous year . In the final series against the Boston Bruins , Gretzky turned in a virtuoso performance : he set a new NHL record for points in the Stanley Cup Finals with 13 , and the Oilers swept the Bruins 4 - 0 . A notable event in Finals history occurred in Game Four on May 24 . With the score tied 3 – 3 in the second period , a power outage hit the Boston Garden , forcing cancellation of the whole game . NHL President John Ziegler ordered the game to be re - scheduled , and , if necessary , played in Boston after the originally scheduled Game Seven in Edmonton . The Oilers would win the next game ( originally scheduled as Game Five ) back in Edmonton 6 – 3 to complete the series sweep , and capture the team ' s fourth Stanley Cup in five years . All player statistics accrued in the aborted Game Four in Boston are counted in the NHL record books . Wayne Gretzky led all playoff scorers with 43 points , including a league - record 31 assists , in 19 games . For his efforts , he was awarded the second Conn Smythe Trophy of his career . After the Cup - clinching game , Gretzky implored his teammates , coaches , trainers , and others from the Oilers organization to join at centre ice for an impromptu team photo with the Stanley Cup , a tradition since continued by every subsequent Stanley Cup Champion . After the season , Fuhr was awarded the Vezina Trophy as the NHL ' s top goaltender . Fuhr was also selected to the first All - Star Team , and Gretzky was selected to the Second All - Star Team . The 1988 Oilers team established a record in the modern Stanley Cup era with a playoffs win percentage of . 889 . In addition , a Sporting News poll conducted in February 2006 listed the 1988 team as one of the top five professional sports teams of the past 120 years . During the 1988 offseason , rumors swirled around the Oilers that Gretzky was going to be traded prior to the start of the next season . On August 9 , 1988 , Gretzky , along with enforcer Marty McSorley and centre Mike Krushelnyski , were traded to Los Angeles . In exchange , the Oilers received $ 15 million US cash , young star Jimmy Carson , 1988 first round draft choice Martin Gelinas , and the Kings ' first round draft picks in 1989 , 1991 , and 1993 . Pocklington ' s image took an incredible tumble after the trade : he was burned in effigy in Edmonton , and the federal New Democratic Party asked the government to act and block the trade . The Oilers traded the 1989 pick ( Jason Miller ) to the New Jersey Devils for defenceman Corey Foster , then used the 1991 and 1993 picks to select Martin Rucinsky and Nick Stajduhar , respectively . Rucinsky went on to a respectable NHL career after being dealt to the Quebec Nordiques , and Stajduhar only played two games in the NHL . Gretzky ' s departure from the Oilers was acrimonious : he had asked the Oilers to renegotiate his contract in 1987 , and he converted his personal - services contract with Pocklington into a standard five - year player ' s contract with the Oilers in the summer of 1987 . According to the ESPN 30 for 30 series , Gretzky had the option to declare himself an unrestricted free agent after the 1988 - 89 season . This meant he could opt out of the last three years of his contract , and , according to Gretzky , he would be allowed to sign with the highest bidder for his services with no compensation to the Oilers . Pocklington allowed Los Angeles owner Bruce McNall to contact Gretzky on his honeymoon to see if he was interested in relocating to Southern California . During the 1988 season , Pocklington approached Gretzky about renegotiating the contract , knowing if Gretzky went to free agency he would be unable to match offers from richer teams such as the Toronto Maple Leafs and New York Rangers . Pocklington told Gretzky it could mean his departure from the team , but Gretzky , unwilling to give up his chance at free agency , refused to blink , which ultimately led to the trade . None of this was public knowledge at the time , but Pocklington didn ' t want to risk Gretzky leaving town without getting anything in return . The trade was viewed as disastrous for the Oilers . Several of the Oilers considered launching a teamwide strike , and even considered demanding that Pocklington sell the team . Since the trade was announced after the Oilers ' season ticket drive for 1988 - 89 closed , attendance was not impacted in the first season after Gretzky ' s departure , but would noticeably decline in subsequent seasons . The 1988 – 89 season was tumultuous in Edmonton . Mark Messier was chosen to succeed Gretzky as captain . The Oilers plummeted in the standings , finishing with 38 wins and 84 points . They finished 3rd in the Smythe Division , behind the juggernaut Calgary Flames and the reborn Los Angeles Kings , led by Gretzky . In February , the Oilers acquired enforcer Dave Brown from Philadelphia , a move that made the Oilers a more fearsome team physically . Jari Kurri led the team with 44 goals and 58 assists for 102 points , proving his worth as an offensive player without Gretzky . Carson , acquired in the Gretzky trade , led the team with 49 goals and was the only other Oiler to hit the 100 - point plateau . Messier led the team in assists with 61 , and defenceman Craig Muni led the team in plus - minus with a + 43 . Ironically , the Oilers ' first round opponent was Gretzky ' s Los Angeles Kings . The eyes of the hockey world focused on this match - up as Edmonton took a commanding 3 - 1 series lead . But Gretzky and the Kings fought back to force Game Seven , which culminated with the Oilers losing 6 - 3 in Los Angeles . It was the first time since 1982 that the Oilers had been eliminated after only one round . Messier led the team in playoff scoring with 12 points in 7 games . Further proving his critics wrong , Kurri was selected to the Second All - Star Team at the end of the season . Following the 1989 season , Glen Sather stepped down as head coach . He remained on as president and general manager , turning the coaching duties over to longtime assistant John Muckler . During training camp for the 1989 – 90 season , Grant Fuhr came down with a severe case of appendicitis . He missed the first ten games of the season , and when he returned he suffered a shoulder injury that sidelined him for the remainder of the season . This marked the emergence of Bill Ranford as a starter . Four games into the season , Jimmy Carson decided the pressure of playing in Edmonton was too intense and walked out on the team . Sather dealt Carson to Detroit , his home town , for Petr Klima , Adam Graves , Joe Murphy , and Jeff Sharples . ( Sharples would later be traded to New Jersey to re - acquire Reijo Ruotsalainen . ) The trade allowed the Oilers to form a modern - day version of the " Kid Line " , with Graves at centre , Murphy on right wing , and Martin Gelinas on left wing . The season was up and down for the Oilers : they improved on their previous season , finishing with 38 wins and 90 points , good for 5th place overall in the NHL . The season is notable for the emergence of Mark Messier as an acknowledged elite player : he led the team with 45 goals and 84 assists for 129 points , finishing second in the NHL scoring race . Randy Gregg led the team with a + 24 , despite only playing 48 games . In the first round , the Oilers faced the Winnipeg Jets . The Jets proved gritty and hungry and took a big lead in the series . Trailing the series 3 - 1 and trailing Game Five by the identical score , the Oilers miraculously rallied to force Game Six at the Winnipeg Arena , where Kurri scored the game winner in front of a hostile Winnipeg crowd . Game Seven was won by the Oilers , 4 - 1 . In the division finals , the Oilers met the Los Angeles Kings for the second straight season . The result would be different than in 1989 , however , as Edmonton swept the series 4 - 0 , outscoring Los Angeles 22 - 10 . The Oilers met the Chicago Blackhawks in the Campbell Conference Finals and fell behind 2 - 1 in the series . In Game Four at Chicago Stadium , Mark Messier ran roughshod all over the Blackhawks , slashing , elbowing and throwing thunderous checks . Messier finished the game with 2 goals and one assist in a 4 - 2 Edmonton victory , and his performance has been called " one of the most terrifying one - man - wrecking - crew performances in hockey history . " The Oilers tied the series and won the next two games , winning the series and setting up a rematch of the 1988 Stanley Cup Finals with Boston . This series will be remembered for the outstanding goaltending of Bill Ranford , and for Game One of the series which still stands as the longest Stanley Cup Finals game played in the modern NHL . Despite being soundly outshot by the Bruins , the Oilers won the game 3 - 2 when Petr Klima scored on a wrist shot from the right - side boards at 15 : 13 of the third overtime . In Game Two the Oilers were outshot 10 - 2 in the first period , but Ranford held tough and the Oilers led 2 - 1 . Then Jari Kurri took over : on his 30th birthday , Kurri scored 3 goals and 2 assists in what became a 7 - 2 Edmonton win . In Game Three at Northlands Coliseum , the Bruins set a new NHL record by scoring ten seconds into a Stanley Cup Finals game , and never looked back in cruising to a 2 - 1 victory . Game Four was dominated by the Oilers ' top line of Messier , Anderson and Simpson , as the trio accounted for 4 goals and 11 points in a 5 - 1 Edmonton victory . Game Five at the Boston Garden saw Bill Ranford stop 29 of 30 shots , and Glenn Anderson score a goal and an assist in leading the Oilers to a 4 - 1 win . The team had captured its fifth Stanley Cup championship in seven seasons . For his superlative goaltending , Bill Ranford was awarded the Conn Smythe Trophy , but Esa Tikkanen , Kurri and Messier were all strong candidates . Simpson led the playoffs in goals with 16 , and he and Messier shared the points lead with 31 . The Oilers again collected multiple awards after the season . Kevin Lowe won the King Clancy Memorial Trophy for his charity work in Edmonton , and Mark Messier won the first Hart Trophy of his career . Messier ' s closest competition for the award was Boston ' s Raymond Bourque , and he edged Bourque in voting by a single first - place vote . Further proving he had stepped out of the shadow of Wayne Gretzky , Messier was selected to the First All - Star Team , over Gretzky who was named to the Second All - Star Team , in the position of centreman . In all , seven players were a member of every Edmonton Stanley Cup team : Mark Messier , Glenn Anderson , Jari Kurri , Kevin Lowe , Randy Gregg , Charlie Huddy , and Grant Fuhr . The Oilers ' record during this time period was 332 - 166 - 62 ( . 648 ) , and their record in the playoffs was 87 - 28 ( . 757 ) . They set more records , too . Gretzky scored at least a point in fifty - one straight games in 1983 - 84 , an NHL record . Transitional years ( 1990 – 1992 ) . The trade of Wayne Gretzky , and the immediate salary increase he got in Los Angeles , led to a far greater awareness of money matters among players . That , combined with the NHLPA ' s decision to fully disclose salaries of every player in the league , led to a new reality of rapidly climbing salaries in the NHL . This reality began to assert itself over Edmonton in the summer of 1990 . Mark Messier , after winning the Hart Trophy the previous season , sought to have his contract renegotiated . Messier wanted his salary doubled from his current $ 1 . 1 million annually to around $ 2 million per season , putting him ahead of everyone in the league with the exception of Wayne Gretzky and Mario Lemieux . Messier was actually under contract to the Oilers until 1993 : still , this did not stop his agent and father , Doug Messier , from pressing Sather for a new deal . Jari Kurri , unhappy with the Oilers ' offer , did not report to training camp : he chose instead to play the entire season with HC Milano Devils in Italy . Glenn Anderson , who had two more years left on his eight year contract , held out of training camp as well , although he returned once the season started . 1990 – 91 . Randy Gregg was waived prior to the season starting , and he chose to retire rather than report to the Vancouver Canucks , the team that claimed him . Grant Fuhr was suspended for the entire season : he admitted in an Edmonton Journal article that he had a long involvement with drugs , and that he had visited a Florida clinic in 1989 for two weeks to clean himself up ( Fuhr has stayed off drugs since that visit ) . Messier was among the most vocal critics of the suspension : he felt it unfair that Fuhr , who sought help on his own for the problem , might have his career ended by the suspension , and that it may prevent other players with similar problems from coming forward and getting help . In mid - season , NHL President John Ziegler announced that Fuhr ' s suspension had been shortened to sixty games . The season itself was not a great one for the Oilers : they finished with 37 wins and 80 points , good for 3rd place in the Smythe Division . Esa Tikkanen led the team in scoring with 69 points , one ahead of Petr Klima , who led the team with 40 goals . It was the last time to date that an Oilers ' player reached the 40 goal plateau . Klima also led the team with a + 24 . Messier , hobbled by injuries , played only 53 games , but still managed to score 64 points . In the playoffs , the Oilers met the Flames in the opening round . This series is viewed by many as the greatest Stanley Cup playoff series ever played . The teams split the first two games in Calgary , during which Messier flattened Calgary defenceman Ric Nattress with a vicious elbow . Games Three and Four , in Edmonton , were both won by the Oilers . Game Four , a 5 - 2 Edmonton win , is remembered for the viciousness of a brawl near the end of the game , where Dave Brown , in a fight with Flame Jim Kyte , tried to pummel Kyte into the ice . The Oilers returned to Calgary with a 3 - 1 series lead , but the Flames fought back to force Game Six , which was won by Calgary in overtime on a goal by Theoren Fleury . The Flames jumped out to a 3 - 0 lead in Game Seven , and the Oilers called an early timeout , during which Tikkanen chewed out the entire bench . Inspired by the speech , Edmonton fought back , and ended up winning 5 - 4 in overtime on a wrist - shot from Tikkanen on his off - wing . It was Tikkanen ' s third goal of the game , and 7th of the series . The Oilers had suffered several injuries in the series with Calgary , and they met Los Angeles in the next round . The first three games of the series were all decided in overtime , and the Oilers held a 3 - 2 series lead heading into Game Six at Northlands Coliseum . The Oilers again won in overtime , on the heroics of Craig MacTavish . In the Campbell Conference Finals against Minnesota , the Oilers ran out of gas : after splitting the first two games in Edmonton , the North Stars won both games on home ice : the Stars repeatedly slashed Messier on his injured hand , though no penalties were called . Game Five in Edmonton was close , but the Stars prevailed , 3 - 2 , to win the series 4 - 1 and go to the Stanley Cup Finals . Tikkanen led the team in scoring in the playoffs with 10 goals and 20 points . First - year Oilers Anatoli Semenov and Norm Maciver proved to be revelations in the playoffs . Semenov finished with 10 points in 12 playoff games , and Maciver led the team with a + 10 in 18 playoff games . 1991 Off - Season : Mass Exodus . Four Oilers ( 3 for Canada , 1 for Finland ) took part in the 1991 Canada Cup . But the tournament was overshadowed by news reports that the Oilers were going to break up the remainder of their championship core . Rumours surfaced that both Mark Messier and Glenn Anderson were on the trade block , and Adam Graves signed an offer sheet from the New York Rangers , which Glen Sather chose not to match : the Oilers were awarded Rangers ' enforcer Troy Mallette as compensation . ( Graves went on to become a 50 goal scorer in New York , while Mallette only played 15 games in Edmonton . ) Tikkanen was apoplectic , and Messier , upset that the Oilers were willing to let Graves walk , issued a public trade demand during the Canada Cup tournament , saying that if the Oilers were not willing to do what was necessary to keep important players , then he did not want to be there either . ( Graves never scored more than nine goals in a season in Edmonton . Sather lamented in 1994 that if he knew how Graves would turn out , he would never have let him walk . ) John Muckler resigned to become head coach and general manager of the Buffalo Sabres . Assistant Coach Ted Green was promoted to Head Coach . When the Canada Cup ended , the Oilers again had several no - shows for training camp . Tikkanen went home to Finland : after his great playoff , he demanded a renegotiated contract worth $ 1 million per season . Anderson stayed out , trying to either force a huge raise or get out of town . Craig Simpson stayed out , also negotiating a new contract . Grant Fuhr showed up to training camp , although it was publicly acknowledged that he was available in trade offers . Partway through training camp , Fuhr and Anderson were traded to Toronto for Vincent Damphousse , Luke Richardson , Scott Thornton , and Peter Ing . Then Steve Smith , also asking for a hefty raise , was dealt to Chicago for Dave Manson . The Oilers acquired Scott Mellanby from Philadelphia for Dave Brown , who asked to be traded back to the Flyers , and the rights to Jari Kurri , who was subsequently dealt to Los Angeles . Charlie Huddy was left exposed in the waiver draft , and was claimed by Minnesota . He , too , was immediately dealt to Los Angeles . Messier stayed at his off - season home in Hilton Head Island , South Carolina awaiting a trade . ( Messier , a native Edmontonian , had actually been spending his offseasons in South Carolina for some time . ) The five main teams in the bidding war to land Messier were the New York Rangers , New York Islanders , Philadelphia , Chicago , and Detroit . Detroit dropped out of the race when Sather insisted that Steve Yzerman had to be part of any deal for Messier , and Philadelphia dropped out because they did not want to trade Mike Ricci . Finally , one day after the season began , Messier was dealt to the New York Rangers for Bernie Nicholls , Steven Rice , Louie DeBrusk , future considerations , and $ 5 million US . ( Part of Messier ' s desire to move to a new team was his desire to make more money than Edmonton could offer . Foreshadowing the financial issues Edmonton would face for the rest of the decade , Messier went from being paid $ 1 . 1 million CDN a season in Edmonton to an average of $ 2 . 6 million US a season in New York . ) Because of the cash the Oilers received in the Messier trade , the view of people in Edmonton was that it was Pocklington again selling off the team ' s best players to pocket cash for himself . A month into the season , defenceman Jeff Beukeboom was also dealt to the Rangers , to complete the future considerations of the Messier deal , for defenceman David Shaw . Shaw was traded to Minnesota later that season for Brian Glynn . 1991 – 92 . Kevin Lowe was selected to succeed Messier as captain . Simpson eventually agreed to a one - year contract to stay in Edmonton . Tikkanen was at an impasse , as Sather refused to budge on his salary demands , until Peter Pocklington actually got Tikkanen ' s home number in Finland from a CFRN sports reporter , personally called Tikkanen and negotiated a new $ 1 million per season contract . Bill Ranford played the entire season while renegotiating his contract , and by season ' s end he too had a new contract worth $ 1 million per season . Despite the staggering amount of turnover , the Oilers actually produced a comparable season to 1990 - 91 , finishing 3rd in the Smythe Division with 36 wins and 82 points . The Oilers were led by a new first line of Damphousse , Nicholls , and Murphy : Damphousse led the team with 38 goals and 89 points . Norm Maciver led the team in plus - minus with a + 20 , also chipping in 40 points despite only playing 57 games . The Oilers ' offence was balanced , with eight players scoring at least 20 goals . The most surprising 20 goal scorer was fourth - line checker Kelly Buchberger . In the first round of the playoffs , the Oilers again met the Los Angeles Kings . The Kings now boasted five team members who had played on the Oilers ' championship team of 1987 ( Wayne Gretzky , Jari Kurri , Paul Coffey , Marty McSorley , and Charlie Huddy ) in an attempt to re - create the Oilers ' success . Stressing disciplined play , the Oilers split the first four games with the Kings before Tikkanen ' s hat trick in Game Five put the Oilers ahead 3 - 2 . Game Six in Edmonton was a 3 - 0 shutout win for the Oilers , as the high - powered Kings were sent packing . Since the Gretzky trade , the Oilers had now met the Kings four times in the playoffs : the Oilers had won 3 of the 4 series , with a head to head record of 15 - 8 . Next up was the division champion Vancouver Canucks ; the Oilers split the first two games at the Pacific Coliseum , then returned to Edmonton and won both games on home ice . Game Five was a Vancouver victory , but the Oilers returned home and won Game Six , again by a 3 - 0 score . The upstart Oilers were back in the Campbell Conference Finals for the third straight season , facing the Chicago Blackhawks . However , their unexpected run in the playoffs came to a crashing halt , as the Blackhawks dominated every game and swept the series 4 - 0 . Stressing defence , Chicago stymied the Edmonton powerplay , which went 0 - for - 19 . These playoffs were viewed as a coming - out party for Joe Murphy , as he led the team with 24 points in 16 playoff games . Rebuilding years ( 1992 – 2004 ) . By this time , the animosity toward the Oilers in the city of Edmonton was no longer deniable . Due to lingering bitterness over the Gretzky trade , attendance had been on the decline for several years , from an average of 17 , 503 ( arena capacity ) in 1988 - 89 to 16 , 179 by 1991 - 92 . By 1991 - 92 , sellouts were rare , even in the playoffs when the Oilers made the Conference Finals . The Messier trade further exasperated the fan base , and by the summer of 1992 , the season - ticket base had dwindled to under 9 , 000 , and for the first time , talk surfaced that the Oilers might leave town . Also , by this time , the financial discrepancies facing the Oilers versus the richer NHL clubs began to manifest themselves . Although Edmonton ' s fan base is loyal , Edmonton has always been one of the smallest markets in the league . In addition , for many years Edmonton lacked a strong business community capable of supporting the Oilers that other NHL cities possessed . ( Part of the reason for this is that due to being the provincial capital , there was never a need to develop a business community in Edmonton the same way a city like Calgary developed . It was not until many years later that Edmonton began to make its corporate and financial community a priority . ) The fact that the Oilers and other Canadian teams paid salaries in Canadian dollars , whereas American teams paid in more valuable US dollars , was also a disadvantage , particularly as free agency came into the NHL . In addition , Pocklington ' s business empire sank under the weight of recession , scandal , and corruption . Many of the players from the dynasty years continued to play at an elite level well into the 1990s , leading to speculation about how many more Cups the Oilers would have won had Pocklington been able to keep the team together . The Los Angeles Kings , with several former Oilers ( Wayne Gretzky , Jari Kurri , Marty McSorley , and Charlie Huddy ) in 1992 - 93 , first eliminated the Oilers from playoff contention with a 5 - 1 victory at the Northlands Coliseum , then the Kings made a surprise run to the Stanley Cup Finals . Then in 1994 , the Rangers won the Cup with " seven " former Oilers on the roster — Messier ( the first player to captain two different Stanley Cup - winning teams ) , Lowe , Anderson , Graves , MacTavish , Esa Tikkanen , and Jeff Beukeboom ( Messier , Lowe , Anderson and MacTavish had been with the Oilers for their five Stanley Cups championships ) . The Rangers ' Stanley Cup win was the last hurrah for the great Edmonton team of the 1980s . Paul Coffey won a Stanley Cup with the Pittsburgh Penguins in 1991 and played an instrumental role in helping the Detroit Red Wings and Philadelphia Flyers make the Cup Finals , in 1995 and 1997 , respectively . Five of those players - - Gretzky ( 1 ) , Messier ( 12 ) , Coffey ( 29 ) , Kurri ( 50 ) and Fuhr ( 70 ) would make the list of the 100 greatest hockey players in the history of the NHL , published in 1998 by The Hockey News , and along with Anderson were all inducted in the Hockey Hall of Fame . The departures of the stars from the 1980s exposed serious deficiencies in the Oilers ' development system . The Oilers had done a poor job of drafting during the dynasty years , though it had gone unnoticed since their stellar records resulted in them drafting late in the entry draft . Even without this to consider , the younger players hadn ' t had nearly enough time to develop before the core of the 1980s dynasty left town . However , this didn ' t become apparent for a few years ; as mentioned above , the Oilers still had enough heft to make the conference finals two years in a row . However , it was obvious that they were nowhere near being the powerhouse that had dominated the league in the previous half - decade . In 1993 , the Oilers missed the playoffs for only the third time in franchise history , and their first time as an NHL team . They would not return to the post - season for four years , despite the emergence of young centremen Doug Weight and Jason Arnott . Trouble followed the team off the ice as well . For most of the 1990s , the Oilers were desperately trying to stay alive . In 1998 , the team was nearly sold to Houston interests who sought to move the team , but before the sale was finalized , and with just hours left on the deadline , the Edmonton Investors Group , a consortium of 37 Edmonton - based owners , raised the funds to purchase the team from Pocklington , vowing to keep the Oilers in Edmonton . The Oilers received support in this endeavour from the NHL , which had already seen two Canadian teams ( the Nordiques and Jets ) move to the United States earlier in the decade . In 1997 , the Oilers made the playoffs for the first time in five years , and in the first round , they upset the Dallas Stars , who had compiled the league ' s second best record , in an exciting seven - game series . Riding on the hot goaltending of Curtis Joseph , the Oilers completed the upset on a breakaway by Todd Marchant in overtime . Another highlight of that playoff series was on April 20 . Down 3 – 0 with just under four minutes to go in Game Three , the Oilers rallied for three goals in the final three minutes of the third period to tie the game and eventually win 4 – 3 in overtime on Kelly Buchberger ' s game - winning goal . Though Edmonton would lose to the defending Cup Champs , Patrick Roy and the Colorado Avalanche , in the next round , fans were ecstatic about the Oilers ' return to the playoffs . In 1998 , Joseph led the Oilers to another first - round upset . After spotting the Avalanche a 3 – 1 lead , the Oilers held the powerful Avalanche scoreless for eight straight periods en route to winning the series in seven games . Dallas and Edmonton met again in the second round , but this time , the Stars were the victors . This was the start of one of the most unusual rivalries in hockey : between 1997 and 2003 the Oilers and Stars played each other in the playoffs six times , five of them first - round matchups . The only year in which they did not meet was 2002 , when neither team made the playoffs . This streak was not formally ended until 2006 , when the second - seeded Stars ( in the Western Conference ) were eliminated in the first round by the Avalanche , while , for the first time in 16 years , the eighth - seeded Oilers went to the Stanley Cup Finals . On November 22 , 2003 , the Oilers hosted the Heritage Classic , the first regular season outdoor hockey game in the NHL ' s history and part of the celebrations of the Oilers ' 25th season in the NHL . The Oilers were defeated by the Montreal Canadiens 4 – 3 in front of more than 55 , 000 fans , an NHL attendance record , at Commonwealth Stadium in Edmonton . A few days earlier , on November 17 , 2003 , the Edmonton Oilers desperately needed a centre , and signed veteran Adam Oates to a contract . However , the 2003 – 04 NHL season was a disappointment as the Oilers failed to make the playoffs , despite also acquiring centre Petr Nedved from the New York Rangers at the trade deadline as the team went on a late - season surge , staying in the playoff hunt until the end of the season , narrowly eliminated from the postseason . On July 23 , 2004 , the team announced that its American Hockey League affiliate , the Toronto Roadrunners , would play the 2004 – 05 AHL season at the Oilers ' home arena of Rexall Place . The decision , an unusual one for a North America n professional sport s organization , was likely influenced by the expectation that the 2004 – 05 NHL lockout would wipe out the 2004 – 05 NHL season . After a successful year , the Edmonton Road Runners were suspended , and was not revived until 2010 when it became the Oklahoma City Barons . Post - lockout years ( 2005 – present ) . The Oilers struggled with their small - market status for years as big - market teams scooped up high - priced help , but after the wiped - out 2004 – 05 season , the Oilers looked poised to compete again . 2004 – 05 NHL lockout negotiations led to a collective bargaining agreement between the NHL owners and players that included a league - wide salary cap , forcing all teams to essentially conform to a budget , as many small - market teams had been doing for years . Sold - out buildings and a more reasonable conversion rate of Canadian dollar revenues to U . S . dollar payroll in the new millennium have also helped the Oilers to return to profitability . Although Edmonton was one of the last teams to make a big splash in the free - agent market , they were able to acquire the rights to and sign former Hart - and Norris Trophy - winner Chris Pronger from the St . Louis Blues to a 5 - year , $ 31 . 25 million contract , as well as trade for New York Islanders forward Michael Peca , two - time winner of the Frank J . Selke Trophy for best defensive forward . Although the club had to give up Mike York and Eric Brewer to the Islanders and Blues , respectively , fans now hoped the team could at least return to the playoffs , if not to the glory the franchise enjoyed during its mid to late 1980s dynasty era . However , the team suffered again from inconsistency during the first few months of the regular season , especially in goal and on offence . Goaltender Ty Conklin was injured during training camp , and when he returned , was unreliable in net . Nominal backup Jussi Markkanen showed flashes of brilliance , but still was not quite ready for regular NHL goaltending duty . Edmonton even tried third - string goalie Mike Morrison , called up from the East Coast Hockey League , but after a strong start , he too faded . A streaky goal - scoring production led by left - wingers Ryan Smyth and Raffi Torres had trouble putting pucks in the net at times , but Torres did produce back to back two goal games on his 24th birthday , October 8 , 2005 , against the Vancouver Canucks and on October 10 , 2005 , against the Mighty Ducks of Anaheim . Chris Pronger also struggled early on with the rule changes restricting the amount of obstruction and front - of - the - net abuse — Pronger ' s previous specialty — that could be performed without a penalty , while Peca simply had trouble adapting to the Oilers ' system and expectations , desperately underachieving . Many called for head coach Craig MacTavish to be fired ; others wanted a big trade , some miracle . Nothing major materialized , but by the end of December , the Oilers led the Northwest Division with a 22 – 18 – 4 record for 48 points . However , the Oilers remained inconsistent . By the end of January , the Oilers traded for scoring defencemen Jaroslav Spacek from the Chicago Blackhawks and Dick Tarnstrom from the Pittsburgh Penguins , and both defencemen , Spacek in particular , secured their shaky blue line . However , their goaltending was still in doubt , and the Oilers struggled after the Winter Olympic break . But right before Trading Deadline 2006 , the Oilers added 2004 All - Star goaltender Dwayne Roloson from the Minnesota Wild , and speedy forward Sergei Samsonov , a former rookie of the year , from the Boston Bruins . The Oilers gave up a pair of picks for Roloson , and checking centre Marty Reasoner and prospect Yan Stastny ( previously acquired from the Bruins ) along with a 2006 second round draft pick for Samsonov . Reasoner returned to Edmonton after the 2006 playoffs ended . The new acquisitions paid off , and Edmonton finished the regular season with 95 points , clinching the eighth and final playoff spot in the Western Conference over Vancouver . Oiler youngsters Ales Hemsky , Shawn Horcoff , and Jarret Stoll led the way in scoring , with break - out seasons of 77 , 73 , and 68 points , respectively . Smyth finished with 36 goals and 66 points , the second - best seasons of his career in both respects . Smyth led the team in goal - scoring , with Raffi Torres next on the list at 27 . 2006 Playoffs . In the first round of the playoffs , the Oilers played the Presidents ' Trophy - winning Detroit Red Wings . Though not given much of a chance by experts around the league , the Oilers embarked on a great Cinderella run , pulling off a six - game upset , neutralizing Wings ' offensive weapons Brendan Shanahan , Henrik Zetterberg and Pavel Datsyuk by using the neutral zone trap . It was the team ' s first playoff series win since 1998 . Edmonton would meet the San Jose Sharks in the Conference Semifinal and were not favoured to win again . The Sharks ' regular season scoring leader Joe Thornton ( also acquired from the Bruins to go to San Jose ) and goal champ Jonathan Cheechoo had just beat the Nashville Predators in 5 games in their previous series . After trailing the series two - games - to - none , the Oilers won the next four , vaulting them into Conference Final . In Game Six , Roloson had a 2 – 0 shutout — his first ever — and Michael Peca netted the game - and series - winning goal . In doing so , the Oilers became the first eighth - seeded team to reach a Conference Final since the NHL changed the playoff format in 1994 . There the Oilers would beat the sixth - seeded Mighty Ducks of Anaheim in five games , claiming the Clarence S . Campbell Bowl for a franchise record seventh time . Edmonton continued their Cinderella run against the Carolina Hurricanes in the Stanley Cup Finals ( marking the first time two former World Hockey Association franchises met in Stanley Cup play — the Hurricanes were previously the Hartford Whalers ) . In the third period of Game 1 , with the score tied at 4 , Oilers blue - liner Marc - Andre Bergeron knocked ' Canes winger Andrew Ladd into Oilers starting goalie Dwayne Roloson , causing an injury to Roloson ' s MCL , knocking him out of the series . With Roloson out , Rod Brind ' Amour scored the game winner on a mix up by Ty Conklin and Jason Smith with only thirty seconds left . After trailing the series 2 – 0 and 3 – 1 , the Oilers forced a seventh game while riding backup Jussi Markkanen , a overtime shorthanded goal in game 5 by local hero Fernando Pisani , and a 4 – 0 shutout win at home in Game 6 . They could not complete the comeback , however , as the Hurricanes won Game 7 by a score of 3 – 1 to capture their first ever Stanley Cup championship . The Oilers , on the other hand , would later hang their 23rd banner in their young history by winning the Western Conference Title . Like the Calgary Flames before them Edmonton failed in a seventh game to win the Stanley Cup . 2006 Off - Season . Four days after their loss to the Hurricanes , Chris Pronger surprised Oiler fans and management when he issued a trade request on June 23 , citing unspecified personal reasons . On July 3 , 2006 Pronger was traded to the Anaheim Ducks in exchange for Joffrey Lupul , defensive prospect Ladislav Smid , Anaheim ' s first round draft pick in 2007 , Anaheim ' s second in 2008 , and a conditional first round pick . In addition , many of the Oilers ' 2005 – 06 acquisitions signed for contracts elsewhere : Jaroslav Spacek went to the Buffalo Sabres on July 5 , Sergei Samsonov signed with the Montreal Canadiens on July 12 , and Michael Peca with his hometown Toronto Maple Leafs on July 18 . In addition , enforcer and fan favourite Georges Laraque , despite offering the Oilers a substantial pay cut in exchange for a no - trade clause , wound up signing with the Phoenix Coyotes , and goaltender Ty Conklin , seeking to rebuild his reputation , signed a two - way contract with the Columbus Blue Jackets the following day . The Oilers also lost 2002 – 03 New York Rangers acquisition Radek Dvorak to unrestricted free agency as the St . Louis Blues signed him on September 14 . Despite these losses , many of the Oilers ' core players were re - signed . Playoff heroes and locally born Fernando Pisani and Dwayne Roloson , age 37 , signed as unrestricted free agent s ( UFAs ) on the first day of eligibility , July 1 . Jarret Stoll , Shawn Horcoff and Ales Hemsky filed for arbitration as restricted free agents , but all settled for multi - year deals before their hearings came up ; Hemsky , in particular , signed for six years and $ 24 . 6 million . The Oilers also brought back centre Marty Reasoner , whom they had traded for Samsonov in March , prospect Tom Gilbert from the University of Wisconsin – Madison , defenceman Daniel Tjarnqvist from the Minnesota Wild , and defenceman Jan Hejda from Khimik Moscow Oblast of the Russian Super League , whose rights were acquired from the Sabres for a seventh - round pick . On August 11 , Rangers UFA forward Petr Sykora and the Oilers agreed on a one - year contract . Just over a month later , on September 12 , Joffrey Lupul and the Oilers agreed to a three - year contract worth $ 6 . 935 million . 2006 – 07 . The Oilers posted a 32 – 43 – 7 record , their lowest point total since the 1995 – 1996 season , finishing in 11th place in the Western Conference and missing the playoffs . Throughout the season , the Oilers lost various players to injury and illness . At one point , they had eleven players out of the line - up and had to rely on emergency call - ups to fill their roster . In May 2007 , Daryl Katz offered $ 145 million towards the purchase of the team . Sources close to the " Edmonton Journal " state that , as part of the deal , the team will remain in Edmonton . No negotiations took place as the Board of Directors immediately responded that the Oilers were not for sale . In July 2007 , Katz tried again , this time increasing the offer to an amount over $ 170 million dollars . Katz bypassed the Board of Directors and brought the offer directly to the shareholders . As of January 31 , 2008 , Katz has upped the offer to $ 200M plus $ 100M towards a new arena . Other highlights include : 2007 – 08 . The Oilers started out of the gate very slowly , going 5 - 10 in their first 15 games . They would finish the first half of the season 16 - 21 - 4 . They would , however , turn it around after New Year ' s . With the emergence of young players like Sam Gagner , Andrew Cogliano , Robert Nilsson , Tom Gilbert , and Denis Grebeshkov , the Oilers would finish the second half of the season a remarkable 25 - 14 - 2 in 41 games . This despite missing big free agent signing Sheldon Souray , Shawn Horcoff , Raffi Torres , and team captain Ethan Moreau for the rest of the season . The Oilers finished 41 - 35 - 6 , in ninth place in the Western Conference and only 3 points back of a playoff spot . Expectations were high for the 08 - 09 season . In the off season , Kevin Lowe traded centreman Jarret Stoll and defenceman Matt Greene for the experienced Lubomir Visnovsky of the Los Angeles Kings . He also traded promising young defenceman Joni Pitkanen for the veteran power forward Erik Cole of the Carolina Hurricanes . Lowe also made offers in the off season to sign star forwards Marian Hossa and Jaromir Jagr , although neither deal went through . These moves were uncharacteristic for the Oilers over the last decade , but with new ownership and a new NHL , the Oilers have shown that they can compete in the free agent market for high priced talent . 2008 – 09 . Oilers goaltender Dwayne Roloson set an NHL record for being the oldest goaltender to play 60 games in a season . However , the Oilers failed to qualify for the 2009 Postseason . 2009 Off - Season . The Oilers kicked off the off - season by firing long - time head coach Craig MacTavish and assistants Billy Moores and Charlie Huddy . The Oilers replaced MacTavish by hiring Pat Quinn to be the head coach , Tom Renney as the associate coach and Wayne Fleming as the assistant coach , while Kelly Buchberger was retained as assistant coach . Edmonton drafted the highly touted Magnus Paajarvi - Svensson , as the 10th overall pick at the 2009 NHL Entry Draft . The Oilers then traded fan - favourite Kyle Brodziak to the Minnesota Wild for another two draft picks in the 2009 Draft , which were used to draft Kyle Bigos and Olivier Roy . The Oilers headed into the Free Agency with two key Free Agents in Dwayne Roloson and Ales Kotalik . Edmonton let both Roloson and Kotalik walk , and they subsequently signed replacements , in the form of veteran goaltender Nikolai Khabibulin and a former Oiler , centre Mike Comrie . Khabibulin signed a 4yr / $ 15 million contract , whilst Comrie signed a 1yr / $ 1 . 125 million contract . While the Oilers made these transactions , their whole off - season was marred by the huge blockbuster trade that was made with the Ottawa Senators , in which the Oilers would acquire ( 2 - time 50 goal scorer ) Dany Heatley , in exchange for forwards Andrew Cogliano , Dustin Penner , and defenceman Ladislav Smid . However , Heatley would refuse to be dealt to Edmonton ( as per the stipulation of his contract ) , and would be later traded to the San Jose Sharks . 2009 – 10 . The 2009 – 10 season did not bring welcoming thoughts to Oilers fans , as Edmonton ended the season with one of the worst records in franchise history : finishing dead last at 30th place , with a total of 62 points . The Oilers ' campaign was blighted by long - term injuries to key players , notably starting goaltender , Nikolai Khabibulin and winger Ales Hemsky ( amongst others ) . The Oilers recorded a total of 530 in current man games lost , a new ( albeit un - wanted ) franchise record high . Dustin Penner emerged as the leading point scorer ( 63 ) , recording career highs in all offensive categories . Penner was one of three Oilers that played in all 82 games of the 2009 – 10 season . 2010 Off - Season – present . On June 22 , 2010 , the Oilers announced that Tom Renney was to be their Head Coach for the upcoming 2010 – 11 season , with Pat Quinn taking an upstairs role , as Senior Hockey Advisor . On June 25 , 2010 , the Oilers made their first ever first overall draft selection the 2010 NHL Entry Draft . Two forwards led the pack of young players as the potential first overall draft pick , Taylor Hall and Tyler Seguin . Oilers ' staff kept the secret of who they were selecting all the way up until the official announcement was made . The Oilers selected Taylor Hall , ending the drawn out debate that earned the nickname , " Taylor or Tyler ? "