Top 5 Heartbreaking Montreal Canadiens Losses Since 1993 Stanley Cup

It’s only 17 games into this young, admittedly shortened season, and yet the Montreal Canadiens have arguably already suffered at least two heartbreaking losses.

Against the Buffalo Sabres on Feb. 7, they gave up a two-goal third-period lead, including the game-tying marker with under two seconds left, ultimately losing 5-4 in a shootout.

And just this past Thursday, aiming for an unprecedented six-game winning streak this year (unless you’re the Chicago Blackhawks…or San Jose Sharks), the Habs gave up another two-goal lead, losing to John Tavares (and 18 other guys, I guess) 4-3 in overtime.

Nevertheless, the Habs and their fans will soldier on somehow. The team, after all, is now in its 19th season since winning its 24th championship. As such, as heartbreaking as the above games were, there are plenty more where they came from, ones that have even made grown men cry.

I mean, just where were the high stakes? The playoff implications? The crushed Stanley Cup dreams? The rioting afterward? Oh, wait, we’re talking losses. Not single-series victories. My bad.

In any case, here are the top five heartbreaking Habs losses since 1993:

5) April 26, 2006: Game 3 of Eastern Conference Quarterfinals

Carolina Hurricanes 2 at Montreal Canadiens 1 (OT)

This series, which Montreal ultimately lost 4-2, resulted in the Habs being dropped by an eventual Stanley Cup-winning team. While Game 3 of their 2005-06 opening-round series against the Carolina Hurricanes wasn’t the deciding game, it was the one in which everything went wrong.

Leading 2-0 in the series after two impressive road victories, seventh-seeded Montreal was in the driver’s seat and looking to pull off an improbable upset heading home. However, with Carolina down 1-0 in the third period, then-captain Rod Brind’Amour tied it up and future captain Eric Staal notched the game-winner in overtime.

To make matters worse, Montreal captain Saku Koivu suffered a serious eye injury earlier in the game, putting the Habs at a serious disadvantage the rest of the series with an injury so sever that it risked the future of his entire career.

If only Montreal had been able to get that elusive third game under its belt, it would have been near-impossible for the Hurricanes to come back. But the Habs didn’t and the Hurricanes did.

Montreal ended up losing the final four games of this series, including this one, with Cristobal Huet giving up an embarrassingly easy goal to stop in overtime in Game 6 (skip to the 1:20 mark of the video) to send the Hurricanes on their way to becoming the league’s first champions following the 2004-05 lockout. It could have been Montreal, folks. Sob.

4) April 23, 2004: Game 3 of Eastern Conference Semifinals

Montreal Canadiens 3 at Tampa Bay Lightning 4 (OT)

After rallying from a 3-1 series deficit for the first time in team history in the first round by beating the second-seeded Boston Bruins, the seventh-seeded Habs found themselves in familiar territory, down two games to none against the Tampa Bay Lightning. However, this time around, there would be no miraculous comeback.

The Habs trailed 2-1 heading into the third period, but Michael Ryder and Patrice Brisebois scored late in the game to give the Habs their first lead of the series with just under four minutes to go. Of course, this was the Tampa Bay team that ended up winning the Stanley Cup, and they clearly weren’t going to go away quietly. I mean, the word “lightning” is in their damn name, for crying out loud.

So, as if you don’t already know, Vincent Lecavalier tied it up with 17 seconds left off of what normally should have been the final faceoff of the game. Then, just over one minute into overtime, and all the momentum with Tampa, eventual Conn Smythe Trophy winner Brad Richards banked it in off goalie Jose Theodore from behind the net.

Yep, Montreal down 3-0 against the soon-to-be champs. The Habs, after this one, just had no fight left in them, and everyone, including their fans, knew it (as much as they didn’t want to believe it).

Montreal, unlike the Lightning, would go gently into that good night, losing the final game of the series 3-1 without much resistance, folding like cheap Bell Centre seats after giving up an initial lead.

With that, the Habs left a sour taste in fans’ mouths for over a year, with the 2004-05 season—the year Montreal was clearly going to win it all, by the way—being cancelled due to the lockout. Ah, the memories.

3) April 7, 2007: Last Game of the 2006-07 Regular Season

Montreal Canadiens 5 at Toronto Maple Leafs 6

No one was really expecting the 2006-07 Montreal Canadiens to win the Stanley Cup—well, not realistically at least. Case in point, any fantasies to that effect would have had to have Cristobal Huet winning not just one but four playoff series…in a row!

Joking aside, this game marked Huet’s first start since returning from an injury. When he was away, a young buck by the name of Jaroslav Halak captured the hearts and minds of Habs fans everywhere in the process (remind you of anything?), keeping Montreal’s playoff hopes alive by compiling a 10-6 record overall.

Yet despite Halak’s heroics, when push came to shove, the Habs opted to go with their de facto starter (seriously, remind you of anything???) in this do-or-die game in which Montreal needed a victory to secure a playoff berth. The fact that this loss came against the rival Toronto Maple Leafs, who themselves were in a position to make the postseason, simply adds to its legend.

Down 3-1 in the second period, Montreal stormed back with four straight goals, taking an eventual 5-4 lead into the third. Following a needless Steve Begin double-minor high-sticking penalty at the 20:00 mark of the second, though, Toronto scored to tie it early in the final frame.

With Saku Koivu off soon thereafter for tripping, the Leafs took their final lead of the game, winning it 6-5 and moving into the eighth spot in the conference…only to be pushed out by the New York Islanders the following day.

It’s worth mentioning that the Islanders gave up a late third-period two-goal lead against the New Jersey Devils, including the tying goal in the dying seconds, but still ultimately won it in a shootout.

Had New York lost, Toronto would have made their sole postseason appearance since before the last lockout. Well, the one before this last one, I should say. Meaning eight whole years ago. Meaning, in turn, the Leafs haven’t made the playoffs in a really long time. That always helps Habs fans cope with this loss slightly less painfully.

2) May 13, 2002: Game 6 of Eastern Conference Semifinals

Carolina Hurricanes 8 at Montreal Canadiens 2

Montreal was supposed to be a team of destiny in 2002.

Saku Koivu was diagnosed with cancer to start the year, only to come back with a few games left in the regular season and inspire the team to make the playoffs by the skin of its teeth.

If that wasn’t enough, Richard Zednik got concussed via a Kyle McLaren clothesline in the opening round, and yet the Habs were still able to hold off the top-seeded Boston Bruins and pull off the incredible upset.

However, then came the seemingly innocuous Carolina Hurricanes in the second round. The Habs were actually in a good position, once upon a time in this series. After dropping Game 1, they won two straight and were up 3-0 in the third period of Game 4, ready to punch a ticket to the Eastern Conference finals against the Toronto Maple Leafs. It was pre-ordained, one might say.

Enter former (and current) head coach Michel Therrien.

After Stephane Quintal got called for cross-checking, Therrien argued the call, saying Quintal was just trying to protect goalie Jose Theodore. No dice. Therrien persisted and got a penalty for abusing the official. On the ensuing power play, Sean Hill scored to put the Hurricanes on the board.

Bates Battaglia scored midway through the period and Erik Cole—you know the name but not necessarily the player this year—scored the game-tying goal in the final minute to send it to overtime. Niclas Wallin then scored the game-winner a few minutes in, and Carolina went on to win the final three games of the series, including their infamous series-clinching 8-2 victory.

Technically, Game 4 could justifiably make this list, but Game 6 grabs this spot just for the sheer embarrassment of losing a playoff game, a series-clinching game no less, by six goals.

By the time Game 6 was four minutes old, it was already 2-0. After 20 minutes, it was 5-1. By the time Doug Gilmour got whistled for tripping in the second (which led to another Carolina goal) in addition to a misconduct for (incredibly) breaking the glass to the penalty box door, the game was essentially over. The dream, just like the glass on the penalty box door, was shattered.

1) December 2, 1995: Patrick Roy’s Last Game

Detroit Red Wings 11 at Montreal Canadiens 1

Another regular-season game, but this one didn’t technically involve the playoffs. However, it did arguably prevent the Habs from making any noise therein for the following eight seasons by indirectly leading to the trade of franchise goalie Patrick Roy.

In the game in question, Roy was finally, mercifully pulled in favor of Pat Jablonski (something that, under normal circumstances, would never otherwise be uttered, ever) in the second period of the widely documented 11-1 home loss to the Detroit Red Wings after giving up nine goals.

Humiliated, Roy walked over to team president Ronald Corey from on the bench and told him he had just played his last game for the Montreal Canadiens. He was traded four days later to the Colorado Avalanche (formerly the hated Quebec Nordiques) with captain Mike Keane for Andrei Kovalenko, Martin Rucinsky and Jocelyn Thibault, thereby setting the franchise back a decade.

The trade on paper wasn’t horrible, but everyone knew it wouldn’t work out. For example: Roy went on to win two Stanley Cups with the Avalanche. Montreal? Not so much.

A young, upstart goalie at the time, Thibault went on to enjoy modest success…with the Chicago Blackhawks, ultimately losing his job in Montreal to a 37-year-old Andy Moog.

Like his hairline, Rucinsky’s production would recede over his seven seasons with the team. And Kovalenko wouldn’t be nearly as lucky, lasting just the rest of 1995-96 season with Montreal before being traded for Scott Thornton.

The 11-1 loss was bad enough (for the record, whenever Mathieu Dandenault scores against you twice in a game, it’s bad enough), but the repercussions from that one loss tainted Roy’s reputation as a professional hockey player and Montreal’s luster as a professional franchise moving forward.

Thankfully, Roy and the team have since made up and his jersey now hangs in the Bell Centre rafters, but no one can predict just how much better off the Habs of the mid-90s would have been had this game gone any other way. The only thing that is for certain is that it wouldn’t have been any worse. Kinda impossible.