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A history of the Flyers and Canadiens playoff matchups, thus far

From “The Shift”, to the Flyers’ third consecutive Cup Finals appearance in 1975-76, these two teams have had a long history.

Montreal Canadiens v Philadelphia Flyers - Game Five Photo by: Bruce Bennett/Getty Images

As of today, the first round matchups for the Stanley Cup Playoffs have been set, though the Flyers have known their opponent since Saturday night. As the #1 seed in the Eastern Conference (oh it feels so so good to type that), the Flyers will take on the lowest seed from the play-in round, the Montreal Canadiens, who shocked the hockey world by defeating the Pittsburgh Penguins in four games. Montreal were able to outwork a lethargic Penguins team (and were also the beneficiaries of some luck, and poor goaltending from Pittsburgh) and certainly announced themselves to the league that they are a team to be taken seriously (despite selling at the trade deadline thinking they had no shot at the playoffs, which they were correct about but hey, 2020 am I right?).

Though obviously the teams are different in this iteration of their playoff bout, the Flyers and Canadiens have a long and storied playoff history against each other. Throughout the more than half a century of the Flyers’ existence, they have faced Montreal six times (and that will be seven after their 2019-2020 series), with the matchups split into three distinct time periods in the organization’s history. It’s actually a very unique time capsule into Flyers history, much like looking at the Flyers’ matchups in the playoffs against the Buffalo Sabres gives an interesting look into the franchise during the 90’s and early 2000’s.

But, I digress, and to start, we have to look back to the NHL’s expansion...

Philadelphia Flyers v Montreal Canadiens Photo by B Bennett/Getty Images

In the late 1960’s and early 1970’s, the Montreal Canadiens were one of the league’s premier teams. The torch was being passed from an aging Jean Beliveau (he was in his age 39 season in 1970-71) and Henri Richard, to younger players like Guy Lapointe, Jacques Lemaire, and perhaps most importantly, Ken Dryden. Eventually, even more hall of famers would come to the rise in Montreal like Guy Lafleur and Larry Robinson, but needless to say, the Canadiens were near dynastic, and were only challenged at the time of expansion by the Boston Bruins and Bobby Orr.

As we all know, the Flyers were on the come up as the 1970’s began, and they played two playoff series against the Canadiens in the decade, one before and one after their Stanley Cup victories. The first of these series took place during the 1972-73, the season before the Flyers won their first Cup. This series was only listed as the “semi-finals”, based on how relatively small the playoffs were at that point in history. In 72-73, the Flyers won their first ever playoff series against the Minnesota North Stars in the quarterfinals, highlighted by an important game five overtime winner by Gary Dornhoefer.

However, it was unfortunately not meant to be for the Flyers against the Canadiens, who defeated them in five games on route to winning the Stanley Cup. Though Rick MacLeish would win the first game for the Flyers in overtime (which sadly wasn’t pictured in the video above), they wouldn’t win another game in the series. The Flyers were a very good team at that point, but they had yet to re-acquire Bernie Parent, who would prove to be the missing piece the team needed to win the Stanley Cup in 1974 and 1975.

By the time the 1975-76 season rolled along, the Flyers were one of the favorites to win the Cup again, and complete the fabled “three-peat”, and they came awfully close. They defeated Toronto and Boston to reach the Stanley Cup Finals, however, the Canadiens stood in their way, and made quick work of the Flyers, sweeping the series to claim the Cup yet again. As is detailed in the fantastic HBO documentary “Broad Street Bullies”, the NHL establishment at the time, and in particular, the Canadiens themselves, felt as if they needed to win the series against the Flyers, as to “right the ship” of the direction hockey was going, away from the brutish nature of the Flyers. Regardless, the Flyers were defeated and though that series did not spell the end of the Broad Street Bullies, it would be their last Finals appearance of the decade.

As I said in the opening, the Flyers’ matchups in the playoffs against the Canadiens can be best categorized in three distinct periods. Therefore, we now zoom ahead in time to our second chapter: the 1980’s.

Philadelphia Flyers v Montreal Canadiens Wales Conference Finals

The Flyers had made a Stanley Cup Finals appearance in 1984-85 (ultimately as they lost to the dynastic Oilers) and looked poised to do so again in 1986-87. However, first they had to get through the Montreal Canadiens in the Wales Conference Finals.

Game one was a tightly contested affair that may be the most well remembered game of the series (though not of those playoffs, with hindsight). A Flyer victory, 4-3, ensured they would have the upper hand early on, and the game was won in overtime thanks to Ilkka Sinisalo, who scored on a broken play out in front of the net.

In the end, the Flyers would win the series in six games, and would go on to have one of the most memorable Stanley Cup Finals ever against the Oilers yet again.

Two seasons later, the Flyers and Canadiens would yet again square off in a Wales Conference Finals matchup, the last one of the decade in 1988-89. However, this time around it wasn’t to be as the Flyers lost in six games. Though the roster was largely the same, Ron Hextall was not the same goaltender he was in 1987, and the Flyers couldn’t find a way past Montreal, who themselves would lose to the Calgary Flames. You may also remember this series for the vicious hit by Chris Chelios on Brian Propp, and the ensuing retaliation by Hextall.

This then brings us to our third and final segment of Canadiens-Flyers playoff history, the one that is the freshest in our minds (really the only ones fresh in my mind since I wasn’t born yet when all of the other series occurred) which would be the 2000’s.

Montreal Canadiens v Philadelphia Flyers - Game Five Photo by: Michael Heiman/Getty Images

After the most turbulent year in Flyers’ history, 2006-07, the team under John Stevens miraculously bounced back and made the playoffs after compiling the worst record in the NHL the previous season. In a thrilling series against the Washington Capitals, which was also known for being Alex Ovechkin’s first ever playoff series (coming off of a 65 goal season, he was red hot), the Flyers defeated the Capitals in seven games, winning game seven on a Joffrey Lupul goal in overtime. They then matched up in the Eastern Conference semi-finals against, you guess it, the Canadiens. Montreal were the top seed in the Eastern Conference, and were pretty good that year (no duh). They were led by Alex Kovalev, Tomas Plekanec, and Saku Koivu, but were outmatched by the Flyers who defeated them in five games. They managed to get pucks by a young Carey Price at a steady clip, outscoring Montreal 20 to 14 in the series, despite Montreal taking the first game in overtime.

Just a few years later, during the famed 2009-10 Cup run, the Flyers would run into the Canadiens again, this time in the Eastern Conference Finals. We all know what happens in this series. The Flyers won in five games as they steamrolled a tired Canadiens club who had decided to stick with Jaroslav Halak in net. There really wasn’t a reality in which the Flyers were going to lose this series. They had come back from 3-0 down to Boston and the momentum and fate, seemingly, was on their side. The most memorable moment, as we all remember, was a classic Mike Richards special, known only as “The Shift”. It’s never a bad time to roll the clip, so here you go:

And that was the last time the teams have faced each other in the post season.

So overall, the Flyers are 3-3 in playoff series against the Canadiens, and are looking to make it three series wins in a row when they square off in game one on Wednesday. Much of the talk from the Eastern Conference bubble has been about the incredible feat the Canadiens pulled off in defeating the Penguins, but the Flyers will hope to end the Canadiens’ run as they enter round one with the #1 overall seed.

Even though game one starts at 1:00 AM in my time zone, I know I’ll be watching.