Since joining the NHL in 1979, the Edmonton Oilers have played well over 300 postseason games, winning nearly 60 percent of them.
That’s a great record, but it still means that Edmonton has been on the wrong side of the score an awful lot of times. Some of those defeats have been truly ugly blowouts. But it’s the close losses that hurt the most.
Related: Kings Survive Epic Collapse Against Oilers to Take 1-0 Series Lead
Unfortunately for the Oilers, they suffered just such a defeat in Game 1 of the 2025 Stanley Cup Playoffs first round on Monday (April 21), when they managed to erase a four-goal deficit and make a stirring third period comeback, only to concede the deciding goal in the final minute of a 6-5 loss to the Los Angeles Kings at Crypto.com Arena.
It was one of those games that Oilers fans won’t want to remember, but they’ll probably never forget. But as much as it stung in the moment, even Monday’s loss doesn’t quite make the cut to rank among the most painful losses in Edmonton’s Stanley Cup Playoff history. Here are the top four:
4) 2006 Stanley Cup Final, Game 1
Everything was going great for the Oilers in Game 1 of the 2006 Stanley Cup Final at RBC Center. Edmonton had jumped on the Carolina Hurricanes, and was leading 3-0 with under three minutes remaining in the second period. But then Carolina erupted for four goals in a span of 12:45 to take a 4-3 lead with less than 10 minutes to play in the game.
The Oilers, however, managed to pick themselves up off the mat and responded with a power-play goal from Ales Hemsky at 13:31 to level the scoreboard at four goals apiece. Then disaster struck.
Moments after Hemsky scored, Edmonton blueliner Marc-Andre Bergeron sent Carolina’s Andrew Ladd crashing into Dwayne Roloson. The Oilers goalie was shaken up and had to be taken to the dressing room, with Ty Conklin taking over between the pipes. Conklin came into the game ice-cold, having not seen a second of game action since Edmonton’s regular season finale, seven weeks prior. Carolina jumped on the opportunity, and Canes forward Rod Brind’Amour scored at 19:28 to lift his team to a 5-4 win.
Things got even worse for Edmonton after the game, when it was revealed that Roloson had injured his right knee and was done for the series. The veteran netminder had been the biggest reason for Edmonton’s Cinderella run to the championship round, and the loss of his services was a devastating blow to the underdog Oilers.
Jussi Markkanen took over in net for the Oilers and performed admirably. The Finnish netminder even managed to backstop Edmonton to Game 7 of the Final, but the Oilers ultimately came up short, losing the deciding contest by a score of 3-1 at RBC Center. Nearly two decades later, the question of “what if Roloson hadn’t gotten hurt” still haunts Edmonton.
3) 2024 Stanley Cup Final, Game 7
Edmonton appeared dead in the water after losing the first three games of the 2024 Stanley Cup Final to the Florida Panthers. The Oilers had been vastly outplayed by Florida, and now faced the toughest task in sports, trying to rally from a 3-0 series deficit.
But Edmonton completely turned the series around, improbably reeling off three consecutive victories, and doing so in dominant fashion, winning Games 4 through 6 by an average margin of 4.33 goals. That set the stage for the winner-take-all Game 7 at Amerant Bank Arena on a hot South Florida night in late June.
The Oilers were so close they could taste it. One win from their first championship since 1990. All of Canada, which hadn’t seen a team drink from Lord Stanley’s mug in more than 30 years, was backing Edmonton.
Game 7 was as tight as you’d expect given everything that was riding on the line. There were just 45 shots on goal between the two teams, and a total of only three penalties called by the officials. Florida’s Carter Verhaeghe and Edmonton’s Mattias Janmark traded first period goals before Sam Reinhart gave the Panthers a 2-1 lead in the second period, and that was it for the scoring. Florida was able to protect its one-goal lead in the third period, frustrating the Oilers who couldn’t break through for the tying goal.
To give an idea of how distraught Edmonton was to have made it so far only to come up just short, Oilers captain Connor McDavid wouldn’t even come out to accept the Conn Smythe Trophy, which he had been awarded as most valuable player of the postseason, following the game.
2) 1982 Smythe Division Semi-Final, Game 3
Game 3 of the 1982 Smythe Division Semi-Final between the Oilers and Kings at the Great Western Forum is so iconic that it has its own nickname, the “Miracle on Manchester”. Regrettably for Edmonton fans, it’s iconic for all the wrong reasons as far as the Oilers are concerned.
The teams had split the first two games of the best-of-five series, which was a bit of a surprise given Edmonton had finished 48 points ahead of Los Angeles in the regular season standings. Now the heavily favoured Oilers were looking to snatch back home advantage inside the historic arena on West Manchester Boulevard.
Everything was going accordingly for the Oilers, who dominated the first 40 minutes and took a 5-0 lead into the second intermission. Then everything went sideways for the visitors.
Los Angeles scored five times in the third period, including three goals in the final 5:22. Steve Bozek banged home a rebound past Oilers goaltender Grant Fuhr with just five seconds left to tie the game at 5-5 and force overtime. Then Daryl Evans scored the game-winning goal for Los Angeles at 2:35 of sudden death.
Not only did Game 3 set the record for the biggest deficit ever overcome for victory in NHL postseason history, but it proved to be the difference in the best-of-five semi-final, as Los Angeles went on to win in five games, establishing the record for biggest series upset (based on regular season point differential) in Stanley Cup Playoff history.
1) 1986 Smythe Division Final, Game 7
Edmonton entered the 1986 Postseason looking to win its third consecutive Stanley Cup. After easily sweeping past the Vancouver Canucks in the division semi-final, the Oilers had their hands full with the Calgary Flames in Round 2.
While Edmonton finished with 34 more points than Calgary in the regular season, the Flames were always one step ahead in the playoffs: Calgary led the series 1-0, 2-1 and 3-2 before Edmonton won Game 6 to force the seventh and deciding contest.
That theme continued in Game 7 at Northlands Coliseum, where the Flames took a 2-0 lead before Edmonton responded with goals from Glenn Anderson and Mark Messier to tie things up at 2-2 heading into the second intermission.
What followed in the third period is the most infamous moment in Oilers history. Just past the five-minute mark, young Oilers defenceman Steve Smith — who was turning 23 that date — attempted a pass from behind his net that hit the leg of an unsuspecting Fuhr and went right into Edmonton’s net.
Suddenly trailing 3-2, the shell-shocked Oilers couldn’t find the equalizing goal as the clock ticked down. Calgary held on to win, ending Edmonton’s dream of a three-peat and handing the Oilers what proved to be their only series loss over a five-year span between 1984 and 1988. The sight of a devastated Smith in tears on the Oilers bench will never be forgotten in Edmonton.
The Oilers will hope their latest heartbreaking playoff loss isn’t a bad harbinger like so many have been in the past. Game 2 between the Oilers and Kings is set for tonight at Crypto.com Arena.
