Four times hockey world just missed out on Leafs-Canadiens playoff matchup

Sheldon Keefe and Travis Dermott discuss how nice it is to know that the Canadiens are their first round opponents, but are more focused on getting their players back healthy for the final 2 regular season games, and to be completely playoff ready.

It’s the all-time hockey missed connection, and people still wistfully indulge the fantasy as if flipping through correspondence with a long-ago lover.

What would have happened if the Montreal Canadiens and Toronto Maple Leafs met in 1993?

Even with all the imaginary ink that’s been spilled over this, it’s hard to overstate the fact that the Habs and Leafs came within a single Toronto overtime goal of going head-to-head for the Stanley Cup on the 100th anniversary of this country’s most cherished piece of silver bling. It seems so unimaginable looking back, even down to the fact the eastern-based squads were somehow in different conferences, thus creating a scenario where they could actually meet in the Stanley Cup Final to begin with.

Now, for the first time since 1979, the NHL’s oldest clubs will collide in the first round in front of zero fans with reason to believe it could be a short series — and people are still going to lose their minds. That’s all you need to know about the magnitude of the rivalry.

Because the ’93 near-miss looms so large, it sort of blots out the fact these clubs have actually come very, very close to meeting in the playoffs on a few occasions since then. They also played what amounted to a play-in game — or, at the very least, a can’t-lose game — 15 years ago.

Since the Doug Gilmour versus Patrick Roy scenarios have been hashed out to death, here are a few more close calls to chew on.

Cujo versus Theo

The Habs entered the 2001-02 season having missed the playoffs for three straight years, representing the team’s longest absence from post-season play since the 1920s. The Canadiens had a very average club, but two big things changed the vibe around the team that spring: Jose Theodore’s Hart Trophy-winning play down the stretch and Saku Koivu’s intensely emotional return to the ice from a months-long battle with cancer.

The Canadiens were locked into the eighth seed entering the final weekend of the season, meaning their first-round opponent would be whoever claimed top spot in the Eastern Conference. A Toronto team in the final season of the Curtis Joseph era had a crack at the No. 1 rank heading into Game 82 and did, in fact, put two points in their pocket with a win over the Ottawa Senators. That gave Toronto — for the first time in franchise history — 100 points on the year and the Buds would have been the top seed had Boston failed to win its final game. The B’s, though, took care of business and nudged the Leafs out by a single point, finishing with 101.

The sneaky-big Montreal-Toronto “what if” of the past 40 years is the fact that, after barely missing each other in Round 1, they came deceptively close to meeting in the East final — when Gilmour was wearing No. 93 in red, white and blue. Toronto won its second-round series versus Ottawa, and Montreal — after shocking Boston in Round 1 — held a 2-1 series lead on Carolina and were up 3-0 on home ice in the third period of Game 4. A 3-1 series stranglehold was fewer than 20 minutes away when coach Michel Therrien blew a gasket over a cross-checking call on Habs defenceman Stephane Quintal and — thanks to his tirade — put his team down two men for a full two minutes. Carolina scored a power-play marker to get off the schneid, made it 3-2 with 7:17 to go and tied the game with 41 seconds left to force overtime, where Niclas Wallin was the hero. The Canes blasted Montreal in Games 5 and 6, before squeaking by the Leafs to win the East.

Last shot wins

While they haven’t met in a playoff series for nearly a half-century, the Habs and Leafs squared off on the final Saturday of the 2006-07 regular season with a playoff berth on the line. Here’s the scenario: the Canadiens and Islanders were tied with 90 points, occupying slots eight and nine in the East. Toronto sat one point back in 10th, with 89. We won’t get into tie-breaker scenarios from 14 years ago – let’s just say, both teams needed the two points to keep their playoff dreams alive.

What do you get when you mix flawed, desperate teams with crease appearances from Cristobal Huet, Jean-Sebastien Aubin and Andrew Raycroft? One wild ride.

Playing at home, Toronto went up 3-1 less than two minutes into the second frame. Michael Ryder made it 3-2 36 seconds later and proceeded to score a natural hat trick in fewer than six minutes of game time to give Montreal a 4-3 lead, which became a 5-3 advantage when Chris Higgins scored his second of the game seven minutes later. Carlo Colaiacovo netted the final tally of a six-goal second period and the Leafs were back in the lead before the third period was four minutes old. Miraculously, nobody allowed another goal the rest of the way and the Leafs eliminated the Habs from playoff contention with a 6-5 victory.

Now Toronto needed second-seeded New Jersey to hold the Islanders to one point or less on Sunday afternoon. Things looked bleak for the Blue and White, as the Islanders carried a 2-0 lead into the final five minutes. But after Jersey cut the lead to one, Toronto boy John Madden tied the game with 0.8 seconds left in the third, forcing overtime and, eventually, a shootout. The dream died on a Wade Dubielewicz poke-check, as the Islanders escaped by the skin of their teeth with the two points they needed to get into the big dance.

Unlucky No. 13

The last time we had an NHL season start in January — teams played 48 games in 2012-13 thanks to the second lockout in eight years — marked the first time of the salary cap era that Toronto cracked the post-season. You may recall something involving the Bruins, Game 7 and the incredulous refrain, “It was 4-1!”

That scarring memory only occurred because a Montreal team that finished 28th overall the year prior surprisingly edged out Boston for top spot in the Northeast Division. Montreal beat Toronto 4-1 in the final game of the season for both teams to finish with 63 points.

Boston, meanwhile, lost its final contest to Washington, ending the year with 62 points. The one-point difference made Montreal the No. 2 seed, while Boston fell to No. 4 in the final year of the conference-based format that ranked the three division winners 1-2-3. Of course, Toronto finished fifth, setting up the first-round tilt with Boston.

Had the Bruins won their final game — or had the Leafs beaten Montreal in their last regular-season game — we would have seen a first-round battle between the Habs and Buds. Instead, the Leafs experienced the horror of Game 7 in Boston and Montreal was waxed in five games by Ottawa.

New Eras

Admittedly, this one is a stretch, but let’s re-visit the first season of the Marner-Matthews era. 2016-17 was also Year 1 for Shea Weber in Montreal following the world-rocking one-for-one involving Nashville and P.K. Subban.

It feels like Tampa Bay and Boston have ruled the Atlantic for a generation, so you could probably win a bar bet (God, I wish) or two by noting the Florida Panthers won the Atlantic in 2016, followed by Weber and the Habs in 2017. As the second-best division winner, Montreal drew the first wild-card team, a New York Rangers squad that actually only finished one point behind the Habs (103 to 102). The kids in Toronto snagged the second wild card and final playoff berth with 95 points, drawing Metropolitan-winning Washington.

Both the Leafs and Habs lost their 2017 first-round series in six games. Neither has won a best-of-seven set since then, but one of these teams will soon change that in the best way possible — at the expense of their oldest rival.

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