The Edmonton Oilers finished their 2023–24 one win away from the Stanley Cup. After a furious start to free agent frenzy, the team looks poised to not just run it back next season but are going into 2024–25 as bona fide favourites with new additions and a top-six that might very well be one of their best groups in the Connor McDavid era. Now, the team is set to usher in a new era with Stan Bowman at the helm to fill out the roster and retain the core. He got off to a strong start with the re-signing of Leon Draisaitl.
Whether or not they set new franchise records in the regular season for winning streaks remains to be known, but the hope with their roster construction is that they go into the season as leaders in the Western Conference and remain atop the league for much of the year. Avoiding the need to come back from a 2–9–1 start isn’t just ideal, at this point, it feels more likely that this team would see a 9–2–1 start instead.
Of course, this isn’t meant to be an early prediction or a hot take in August turned cold take by November. This is just the reality of the Oilers right now and what they should be expecting of themselves. They’re a clear-cut playoff team and should be contending for the division and conference crowns in the regular season.
One thing they’ll want to do differently in 2024–25 once the playoffs come around? Not lose to the eventual Cup winner.
The Oilers have been on the wrong end of a playoff trend
Over three straight seasons, the Oilers bowed out in the playoffs to the eventual Cup winners. In 2022, they were swept by the Colorado Avalanche in the Western Conference Final; in 2023, they lost to the Vegas Golden Knights in six games, this time in the second round. And of course, we all know what happened this year with their 15-win postseason and miracle Stanley Cup Final comeback that came one win short.
That’s three straight seasons where the Oilers’ final handshake lines involved them watching the very team that beat them go on to lift the Cup. The number of “what ifs” and “what could have beens” for the Oilers has surely reached an all-time high.
Just how rare is it in the NHL to make the playoffs and lose to the eventual Cup winner over three consecutive seasons? Let’s take a look.
Teams with consecutive playoff losses to Cup champions
If you’re going to lose in the playoffs, losing to the eventual Cup champions might take the sting away for some or ignite a fire for others. For the Oilers, they became just the sixth team since the NHL switched to a 16-team playoff format in 1980 to lose to the Cup champions over three consecutive years.
Here are the six teams that have been ousted in these circumstances.
| Team | Streak Years | Cup Winners |
|---|---|---|
| Edmonton Oilers | 2022, 2023, 2024 | COL, VGK, FLA |
| Vancouver Canucks | 2010, 2011, 2012 | CHI, BOS, LAK |
| Philadelphia Flyers | 2009, 2010, 2011 | PIT, CHI, BOS |
| St. Louis Blues | 1997, 1998, 1999 | DET, DET, DAL |
| Boston Bruins | 1990, 1991, 1992 | EDM, PIT, PIT |
| New York Rangers | 1981, 1982, 1983 | NYI, NYI, NYI |
As seen, this is the first time a team has seen this outcome in over a decade—the last team before Edmonton was the Vancouver Canucks. Astonishingly, the Philadelphia Flyers’ streak overlapped with the Canucks as well, with both teams being beaten by the Chicago Blackhawks and Boston Bruins in consecutive years. The fact that Vancouver and Philadelphia are in entirely different conferences makes this a crazy overlap.
Before these teams, the other three instances occurred in the previous century with the St. Louis Blues, Boston Bruins, and New York Rangers facing such three-year losing streaks themselves in an entirely different era of NHL hockey.
The Bruins had some poor luck, as their three-year losing streak to the eventual Cup champs was part of a run of four out of five seasons. They also lost to the Oilers in 1988, but they did not lose to the Calgary Flames—the 1989 Stanley Cup Champions.
However, the Blues had an even worse run, losing to the eventual Cup champions five times over six years. Their three-year streak to cap was paused in 2000 when the New Jersey Devils won the Cup—beating the Dallas Stars in the Cup Final as the West’s representative. During this time, St. Louis was a playoff team but they weren’t quite a contender. In 2001 and 2002, they lost to the Colorado Avalanche and Detroit Red Wings, respectively, as those two teams also went on to win the Cup.
Lastly, not to be left out of the fun in this list, the New York Rangers are the only team to have their three-year losing streak be to the same team, as this came during the New York Islanders’ dynasty era.
A rare type of losing streak
Believe it or not, this type of trend is quite rare in the NHL. With the playoff format changing multiple times all while involving 16 teams, as well as the unpredictability of regular season standings and round-by-round playoff seeding, the number of teams with even two straight postseason losses to the eventual Cup winner isn’t that much higher than teams with three losses.
Again since 1980, there have only been 10 teams with two seasons that finished in this manner—the latest team being the New York Islanders losing in 2020 and 2021 to the Tampa Bay Lightning. This makes sense as a Cup winner can only beat four teams a postseason, and the chances of different Cup winners facing the same team are quite low in itself.
So if there are repeat Cup champions like the Lightning, then chances are they’d face different playoff teams over consecutive seasons. Even in Tampa’s eight series wins in 2020 and 2021, they faced seven different teams. Granted the pandemic season did change up some of the potential seedings such as facing a North Division team in the Montreal Canadiens in the Cup Final, which would not happen in a regular playoff bracket.
With 16 teams in the playoffs and the Cup winner only ever facing four opponents, the chances of running into a Cup winner in a playoff series are much lower than facing and losing to another team. So to even string together two consecutive playoff runs that include losing to the Cup winner in both years is evidently rare.
The fact that there have been six teams with three-year losing streaks is more astounding given how few instances there are of two-year losing streaks.
A change of fate
As mentioned, the Oilers’ offseason started fast and furious, with the team having very few days off between their last game of the season and the transition into the NHL Draft and free agency. As they usher in a new era with the departure of Ken Holland, they’ll be looking to make a statement in 2024–25.
What better way to make one than to snap this current streak and become the Cup champs themselves? If the Oilers could manage this, they’d be the first team in this group of six to go from near victory to reaching glory. While they use the offseason to reset and recover, let’s hope they open the next season roaring and ready to make history.
Photo by Curtis Comeau/Icon Sportswire
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