While not the biggest rivalry anymore, the Toronto Maple Leafs and Philadelphia Flyers have had their fair share of interactions over the years. From franchise-altering trades to theatrical line brawls, these two teams have a deep-rooted history.
Flyers – Maple Leafs Notable Trades
The first trade on this list was almost a massive mistake for the Flyers. On Jan. 31, 1971, the Flyers dealt goaltender Bernie Parent and a 1971 second-round draft pick to the Maple Leafs in exchange for netminder Bruce Gamble, center Mike Walton, and a 1971 first-round draft choice. Parent is now in the Hockey Hall of Fame with multiple Stanley Cup championships, so this would look pretty bad on the Flyers’ part if this is where the transaction ended. Thankfully, they made a trade that would reverse what would have been a monumental disaster.
On May 15, 1973, Philadelphia made a trade with Toronto to get Parent back. They received a 1973 second-round draft selection and Parent, while Toronto received a 1973 first-round pick and the rights to Flyers’ starting goaltender Doug Favell. Only a year after this trade, the Flyers became the first expansion team to hoist the Stanley Cup, defeating the Boston Bruins in six games, while Parent won the Conn Smythe Trophy as Playoff MVP with his dominating effort, as well as the Vezina Trophy for being the best goaltender in the NHL during the regular season. Parent won the Vezina and Conn Smythe again the following season, becoming the only goaltender to win both awards in consecutive seasons. That Parent trade remains one of the worst in Maple Leafs history.
On Jan. 20, 1982, Toronto made the decision to deal captain and franchise star Darryl Sittler to the Flyers and received forward Rick Costello, a 1982 second-round draft choice and future considerations that became forward Ken Strong. Displeasure with ownership was the sole reason for this move.
Related: Flyer Trades: Acquiring Darryl Sittler
Sittler actively wanted to leave Toronto, and Philadelphia was on his list of destinations. While Sittler did not help bring a championship to Philadelphia, he did score 84 goals and 94 assists in just 191 games for the club. Overall, Philadelphia ended up getting the best player in the deal.
We have to go to the 21st century to find another impactful trade between these two teams. On June 23, 2012, the Flyers traded winger James van Riemsdyk to Toronto for defenseman Luke Schenn. Both players were drafted in the early first round a few years earlier but neither had necessarily been the star player that was expected of them. Schenn was traded to the organization that had his brother, Brayden Schenn, and could hopefully turn his career around. Unfortunately, this never came to fruition and the defender was traded to the Los Angeles Kings in 2016.
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On the other hand, Toronto landed a steal in van Riemsdyk. In six seasons with the Maple Leafs, van Riemsdyk was a top-six staple and one of the team’s most consistent goal scorers. In 413 games, he registered 153 goals and 291 points. His two 30-goal seasons in Toronto were enough to call this deal a success for the Maple Leafs.
Regular Season Clashes
The Flyers and Maple Leafs have had a few memorable run-ins during the regular season. Notably, goaltenders Felix Potvin and Ron Hextall went at it back in 1996. The underdog by a long shot here was the former, but he held his own and landed quite a few haymakers.
Another one that comes to mind is the line brawl that occurred between the two teams on Dec. 11, 1999. The drama had been brewing throughout the game, and things finally boiled over by the mid-point of the second period. The premier fighters in the bout included Tie Domi, Craig Berube, and Sandy McCarthy, which had less to do with the punches being thrown and more to do with the lack thereof.
Domi was criticized by Flyers’ color commentator Jim Jackson for avoiding an altercation during the brawl. The Flyers seemed to outmatch the Maple Leafs in terms of fighting skill, with Berube and McCarthy, so this makes sense. Regardless, this brawl is timeless and a fantastic watch.
One of the more infamous moments in NHL history came about on March 29, 2001. Domi, serving time in the box for a penalty, had items thrown at him by Flyers fans. In response, he squirted his water over the glass at the fans in retaliation.
Related: This Day in Flyers History: Fan Fights Tie Domi
Flyers fan Chris Falcone charged at the glass and ended up breaking the pane. He fell and was standing in the box with Domi with no restrictions, so Domi and Falcone had a brief tilt before they could be separated. Thankfully no punches were thrown, but this marked what is arguably the peak of the Flyers’ rivalry with Toronto.
Flyers vs. Maple Leafs Playoff Drama
The Flyers and Maple Leafs have met in the playoffs six times, and the Flyers have had their number for the most part.
In 1975, the teams met for their premiere playoff matchup. In the first round, the Flyers handled the Maple Leafs with a 4-0 sweep. Forward Rick MacLeish led the way with four goals in the series for Philadelphia, but the story of the matchup was the team’s excellent defense and the goaltending masterpiece that Bernie Parent put up for the Flyers.
In 1976, Toronto and Philadelphia met in the postseason again. This matchup was much closer, but the 51-13-16 Flyers defeated the 34-31-15 Maple Leafs in seven games. The story of this series was the offense, highlighted by winger Reggie Leach for the Flyers. His six goals and 11 points helped him set the record for most goals in a playoff season with 19, which still stands.
For the third consecutive season, Philadelphia and Toronto met in the first round. The series ended in another win for the Flyers. Darryl Sittler finished the matchup as the highest scorer with 12 points in six games, but Philadelphia’s two overtime wins were vital in helping them win the series in six games.
We would have to wait over twenty years to see these two teams face each other again in the playoffs. In 1999, Toronto was finally able to avenge their demons, defeating Philadelphia 4-2 in the series. Offense was scarce for both sides with a combined 18 goals against in the six-game series. Goaltender Curtis Joseph was a rock for the Maple Leafs, registering a .952 save percentage and a masterful 1.46 goals-against average.
The Flyers got their revenge in 2003. This back-and-forth seven-game series ended with the Flyers on top despite the team losing twice in overtime. Hall-of-Fame forward Mark Recchi led the way for the Flyers with six goals and nine points in the series.
The most recent matchup between these two teams is probably the most memorable, partially because 2004 marked the last time the Maple Leafs had won a playoff series until their victory against the Tampa Bay Lightning in 2023. Toronto and Philadelphia played what was arguably their most evenly-matched series to this point.
In overtime in Game 6 with the Flyers needing a win to advance to the Eastern Conference Final, Maple Leafs forward Darcy Tucker plowed through Flyers winger Sami Kapanen who struggled to get to the bench. The play was not blown dead by officials, so Jeremy Roenick naturally scored the dagger for Philadelphia less than a minute later. This playoff matchup will be one of the greatest in the history of the two teams for a long time.
Future of the Rivalry
Philadelphia and Toronto are now on differing paths, with the Flyers in the midst of a rebuild and Toronto trying to contend for a championship. Even though these teams have not had bad blood for a while, we can hope that they will soon have matchups on a regular basis that are as thrilling as those in in the late 1990s and early 2000s.