NHL teams that lost out in the Cup Final only to win it soon after

You may or may not remember that the Edmonton Oilers lost the Stanley Cup Final in 1983, but it set them on a path to winning five Cups in seven years.
Jun 24, 2024; Sunrise, Florida, USA; Edmonton Oilers forward Leon Draisaitl (29) controls the puck against Florida Panthers defenseman Niko Mikkola (77) during the third period in game seven of the 2024 Stanley Cup Final at Amerant Bank Arena. Mandatory Credit: Sam Navarro-USA TODAY Sports
Jun 24, 2024; Sunrise, Florida, USA; Edmonton Oilers forward Leon Draisaitl (29) controls the puck against Florida Panthers defenseman Niko Mikkola (77) during the third period in game seven of the 2024 Stanley Cup Final at Amerant Bank Arena. Mandatory Credit: Sam Navarro-USA TODAY Sports / Sam Navarro-USA TODAY Sports
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So at the time of writing this it is July 1, which is significant in a few key ways. Not only is it Canada Day, and the start of NHL free agency, but it's also the one week anniversary of the Edmonton Oilers losing in game seven to Florida in the Stanley Cup Final.

Now many of you might be asking - why would I bring this up now? Am I a masochist? No. Believe it or not, this is actually a step forward. NHL history has shown that you must lose in the Cup Final before you can win. It's something you can take the bank. When I made my prediction here, there was literally no doubt in my mind that the Oilers would come out victorious - and if we're being honest, in my defense, they very nearly did, only missing by a mere two goals. But perhaps I was blinded by elation and emotion, not hallmarks of who I am as a sports fan. I thought the McDrai duo, a combination lethal to the opposition, would overcome NHL tradition. But I was wrong.

If Wayne Gretzky and Mark Messier could lose in 1983, then surely Connor McDavid and Leon Draisaitl could lose in 2023. In hindsight I realize that now. I did tip my hat to Florida as opposition when I made my prediction, though, going into the series with my mind wide open knowing full well they were also a good team and could also win it. There was also the very real history of both the regular season and playoffs when the Oilers came back from adversity time and time and time again, so I had that going for me too, as did all Oiler fans.

Last Monday night, a friend of mine was watching the game at his house while I was watching it at mine. (I have a part time job whose schedule is in the late afternoon-early evening, so I was only able to give a portion of the game my full attention). He wanted to go out and see how Whyte Ave. was doing at a time like this, so he drove to my place and we went there and, as expected, was very quiet. There's an ice cream place my friend likes to go on Whyte, and since I'm down on my luck job wise right now he treated me. While we were in line, a guy walked past me saying "blow it up" - not literally, of course, but referring to the team. This is, of course, a sentiment not based on reality or logic - as the smart sports fan judges their team on - but strictly on emotion.

Did it suck to lose last week? Yes it did, even for a less emotional fan like myself. But, is it the end of the world or the start of another rebuild? Absolutely not. The NHL is filled with teams who lost in the Cup Final one year, only to win not soon after. Let's go through some of those teams now:

New York Rangers, 1937 - The New York Rangers lost the Cup final in 1937 to Detroit, only to rebound in 1940 against the Toronto Maple Leafs to win.

Toronto Maple Leafs, 1936, 1940 - The Leafs lost to Detroit in 1936 and to those same Rangers in 1940, before winning it all - against Detroit, no less - in 1942.

Toronto Maple Leafs, 1960 - The Leafs lost in 1960 against Montreal, only to go on to win in 1967 against Montreal. How mad do you think the people of Montreal were that year?

But this was the original six era, you say, where you practically had to bunch your huggies not to make the playoffs? Well, prepare to be amazed.

Calgary Flames, 1986 - The Flames would lose in 1986 - Patrick Roy's first full season in the NHL, no less - to Montreal, only to beat the Habs three seasons later in 1989. This 1989 date in history is also significant as it would later spawn a great joke - "What's the difference between the Calgary Flames and a bra?" "A bra has two cups." Lol, hope you enjoyed that one.

Montreal Canadiens, 1989 - They would lose to the Flames in 1989, only to come back to the Final in 1993 and beat Gretzky and the LA Kings - subsequently the last appearance in the Cup Final of his career.

Detroit Red Wings, 1995 - Ah the neutral zone trap era - this Final likely goes down as one of (if not the) most boring Cup winners to watch in NHL history. Anyway, the Red Wings lost to New Jersey in '95 before winning two straight in 1997 and 1998, starting Ken Holland's legacy as a GM with the golden touch.

New Jersey Devils (reverse order), 2000 - This is a weird one. The Devils won the Cup in 2000, only to get back to the Final but lose in Colorado the next year. How do you think that loss would've felt for Devils fans? Experiencing the thrill of victory before the bitterness of defeat? No other team has really done it in this order since, except for Tampa Bay. But never fear, for the Devils avenged that loss in 2003 when they won against the Ducks. Speaking of which....

Anaheim Ducks, 2003 - The Ducks lost to New Jersey in 2003 before coming back to the Final in 2007 and winning it all against the Ottawa Senators, for the franchise's one and only Stanley Cup win so far. They're still rebuilding at this time, so don't count on them going back to the Final anytime soon.

Pittsburgh Penguins, 2008 - The Pens lost to Detroit in 2008, only to come back from the experience and flip the script, beating Detroit in 2009 then San Jose and Nashville in 2016 and 2017 respectively.

Tampa Bay Lightning, 2015 - The Lightning lost to Chicago in 2015 only to come back and win two straight during the covid era of 2020 and 2021, then would go on to lose against Colorado in 2022 - the other reverse order.

Vegas Golden Knights, 2018 - The Vegas Golden Knights lost in 2018 to Washington only to make it back to the Cup Final in 2023 and beat Florida, which then brings us here.....

Florida Panthers, 2023 - The Panthers lost in 2023 to the Golden Knights, only to beat the Oilers in 2024 to win it.

That's many examples of teams that had to lose before they would win - and that's why they play the games, as the cliche goes. Some teams, like the Blackhawks of the 2010s, were just so loaded at every position they didn't have to lose a Cup Final before winning one. Ditto the LA Kings of the 2010s as well.

Others, like the 1991 and 1992 Pittsburgh Penguins, won their first cup in franchise history in 1991 largely because their opponent was a cinderella story that wasn't supposed to be there in the first place in the Minnesota North Stars. But history shows those teams are the exception, not the rule. It could be much worse - other teams like Ottawa, Nashville, San Jose, Buffalo, and Vancouver have appeared in Cup Finals but have yet to win one.

The million dollar question, though, is this - Will the Oilers repeat Florida's history and win the Cup in 2025 after losing it in 2024? Maybe. As an Oilers fan, I hope so. It may not be next season, but I believe the Oilers are more primed than ever to win a Cup going forward. Gretzky once told McDavid in this interview that he was too good NOT to win the Stanley Cup, and I believe him.

The Oilers WILL win the Stanley Cup, it's just a matter of when, not if. You can quote me on that.