Stanley Cup Rematches: What Other Teams Fought Each Other Twice for the Cup?

Edmonton’s win over Dallas on May 29 set in motion a repeat of last year’s Stanley Cup challengers, with the Florida Panthers punching their ticket to the Final the day before. 

With that in mind, I compiled a list of the five most recent Stanley Cup rematches between two teams. 

For our purposes here, I only considered rematches that occurred within two years of the first meeting in the Stanley Cup Final, apologies to historic rematches like the 2019 Stanley Cup Final between Boston and St. Louis. 

As you’ll begin to notice, the Edmonton Oilers have a history of being in this spot, and they’ve won every one of their recent Stanley Cup rematch opportunities. 

2009 Penguins vs Red Wings

The 2009 Stanley Cup Final between Pittsburgh and Detroit is the most recent example of a Stanley Cup rematch. 

Both teams had met the year prior in a Finals that ended in a six-game Red Wings victory. The 2008 Cup Final was notable for a triple-overtime game in Game 5, which became the fifth-longest game in the history of the championship series. It’s also the last championship for any professional sports team from Detroit. 

In 2009, the Penguins won a seven-game series in the championship, with a close 2-1 victory in the final game. 

In the previous year’s series, the Pittsburgh core of Sidney Crosby, Evgeni Malkin, Kris Letang, and Marc-Andre Fleury was still developing. By 2009, Fleury had evolved into the elite goaltender he is known as today, as evidenced by his save in the final seconds of Game 7 on a Nicklas Lidström rebound shot. 

The Penguins’ other key development that year was a mid-season coaching change, firing 2008’s coach, Michel Therrien, and elevating their AHL head coach, Dan Bylsma. When the move was made, Pittsburgh was out of the playoffs with 25 games to go in the regular season. They quickly rebounded and won the Stanley Cup with Bylsma at the helm. 

1990 Oilers vs Bruins

The 1990 Stanley Cup Final was a rematch of the Final from two years prior between Boston and Edmonton.

1988’s championship was the last for the Oilers with Wayne Gretzky, who would be traded in the following offseason. Edmonton won the series in a technical sweep, but the series result is controversial, given that Game 4 was suspended due to a blackout at the Boston Garden. 

The game was tied when the power went out, and the NHL decided to replay what was technically Game 4 as a fifth game in Edmonton, a game the Oilers ended up winning. This meant the Bruins lost home-ice advantage for one game and then became the only team in history to be swept in five games. 

The core of Boston remained largely the same in 1990, but the result wasn’t much different. They lost, this time in five games, to an Edmonton team that had remade itself with a new defensive identity in Gretzky’s absence. 

The 1990 Stanley Cup was the fifth and final championship for the franchise.

1987 Oilers vs Flyers

You can’t really tell any story about the history of the NHL without repeatedly mentioning Gretzky’s 1980s Oilers. They’re like the Forrest Gump of professional hockey history. They just keep popping up everywhere. 

The 1987 Stanley Cup Final was a rematch of the 1985 Finals, a five-game gentleman’s sweep between an Oilers dynasty in the making and a very inexperienced Flyers team, which had the youngest team in the league, and an average age of 24.5. 

Game 1’s 4-1 Philadelphia blowout was so bad that Edmonton coach Glen Sather allegedly burned the videotape of the game. From there, there was no question who the better team was. 

By 1987, though, the Flyers were significantly better than they had been two years prior. They had become an older, deeper, and more physically tough team. 

Their goaltending situation was one formed out of a tragedy in the fall of 1985, when Philadelphia’s goaltender Pelle Lindbergh died in a car accident. But now in 1987, the Flyers had found a new young goaltending sensation, in Ron Hextall, who, like Lindbergh, won the Vezina Trophy before leading his team to the Cup Final.

Philadelphia battled back from an initial 3-1 deficit in the series, fighting against a tired Oilers team, and grabbing tight victories in Games 5 and 6. In Game 7, the Flyers had an early 1-0 lead but then surrendered three unanswered goals to Edmonton. 

Hextall eventually became the Conn Smythe Trophy winner for series MVP, despite a losing performance. 

1984 Oilers vs Islanders

The 1984 Cup Final represented a changing of the guard of sorts for dynasties in the NHL, serving as a bridge between the Islanders’ dynasty, which had won four straight, and the Oilers’ dynasty, which would go on to win five in seven years. 

The year prior was New York’s fourth consecutive championship, won in four games against a young Edmonton team. Given the breadth of playoff hockey experience the Islanders had by that point in 1983, there was no way the Oilers could win the series. 

In the years following the 1983 Final, Edmonton’s players have repeatedly said that watching the New York team’s muted response to winning another title, most of them more exhausted than excited, was instructive about what it took to become champions. 

In 1984, the Oilers had playoff experience and a defensive focus to complement their high-flying Gretzky offense from the previous year. This year’s result was remarkably different, a dominant five-game victory in which Edmonton won the final three games by three or more goals. 

1978 Canadiens vs Bruins

The 1978 Cup Final between Montreal and Boston were a rematch of the previous year’s Final. It’s one of the only rematches that doesn’t really have a discernible difference from one year to the next. 

The Canadiens in 1977 were at the peak of their dominance in the 1970s. They broke records during the regular season, setting one for the most points, with 132, and another for the most wins, 60. Those have been broken by now, due to changes in overtime rules in the regular season, but they still hold the record for most regulation wins and most points per game. 

The Bruins in 1977 were at the tail end of their contending period, with franchise legend Bobby Orr fading by that point. 

Montreal’s win in 1977 would be their 20th championship in franchise history. 

In 1978, the Canadiens were still strong but no longer as dynastic. While they still beat the Bruins, they took six games to do it, instead of the sweep they achieved in 1977. 

It’s the last time that the two historic rivals ever met in the Stanley Cup Final.