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Detroit Red Wings forward David Perron crashes into Montreal Canadiens goalie Cayden Primeau during the third period at the Bell Centre. The Red Wings won 5-4 on April 16, 2024.Eric Bolte/Reuters

The Detroit Red Wings were knocked out of playoff contention once again on Tuesday night, and it hardly could have come in more gut-wrenching fashion.

Patrick Kane scored the shootout winner in a 5-4 Detroit win over the Montreal Canadiens in their regular-season finale, completing a comeback after a dramatic game-tying goal from David Perron with 3.3 seconds left in regulation.

But it didn’t matter.

The Red Wings entered the night tied with Washington for the East’s second wild-card spot with 89 points, but the Capitals held the tiebreaker over Detroit with more regulations wins.

Meanwhile, Washington was visiting Philadelphia, and the 87-point Flyers needed a regulation win and a Detroit regulation loss to keep their playoff hopes alive.

Just after the Red Wings celebrated Perron’s heroic, game-tying goal, the Flyers, not realizing that Detroit had forced overtime and effectively ended their season anyway, pulled the goalie with three minutes remaining in a 1-1 tie with Washington to attempt a win in regulation.

T.J. Oshie, however, quickly scored into the empty net to give the Capitals a 2-1 lead, and Washington ultimately booked its ticket to the post-season.

“The way it played out, you can’t even make that up,” Red Wings coach Derek Lalonde said.

“It’s hard, it’s gutting, we’re pretty sad in here,” captain Dylan Larkin added from Detroit’s locker room. “This year coming to an end like that, is very, very sad. Very hard.”

Over in Philadelphia Flyers head coach John Tortorella said he became aware of Detroit’s equalizer just after Washington had scored the empty-netter.

“That was the right time to pull (the goalie),” Tortorella told reporters. “Didn’t know anything about what was going on with Detroit at the time, but immediately after that our video guys told us that Detroit just went to overtime.”

Daniel Sprong had a goal and an assist, while Moritz Seider, Joe Veleno and Perron also scored for Detroit (41-32-9). James Reimer stopped 29 shots.

The Red Wings prevailed in a dramatic 5-4 overtime victory over the Canadiens on home ice Monday as Lucas Raymond scored a game-tying goal with the goalie pulled before burying the overtime winner.

And despite pulling off another jaw-dropping comeback on Tuesday, Detroit will miss the playoffs for an eighth straight season.

“We just wouldn’t go away, we wouldn’t die. Comeback after comeback,” said Larkin, who added the Red Wings found out they’d be packing their bags for the off-season before the shootout.

“To hear the way it went down, I guess, that stings. Our group, very resilient, came back in the game and you know, it’s just very unfortunate.”

Brendan Gallagher and Juraj Slafkovsky had a goal and an assist, while Alex Newhook and Cole Caufield also scored for Montreal (30-36-16). Cayden Primeau made 36 saves.

Canadiens fans got a first glimpse of some up-and-coming blueliners in the organization. Logan Mailloux made his NHL debut after spending the entire season with the American Hockey League’s Laval Rocket. The 21-year-old produced one assist for his first NHL point.

Meanwhile, 20-year-old Lane Hutson showed his moves, received loud applause and produced a crucial assist playing at the Bell Centre for the first time. He debuted Monday in Detroit, where he earned one assist.

“The crowd was awesome I kind of feed off of it,” Hutson said. “It’s really cool. I mean they’re some smart fans. They know when a play can happen and you hear it all game, so it’s really special.”

Down 3-2 after 40 minutes, the Red Wings tied the game 3:31 into the third period as Sprong banked a shot from behind the net off Primeau.

Slafkovsky put Montreal back ahead with his 20th of the season, deflecting a point shot from Hutson at 12:46.

With Detroit’s season on the line and the goalie pulled, Perron equalized with a one-timer off an offensive zone draw after a questionable icing call went against Montreal with seven seconds left.

It kept the Red Wings’ season alive, only momentarily.

“It’s crazy, it stings a lot obviously,” Perron said. “From going to look at the clock, there’s seven seconds, and then scoring that goal and then coming back to the bench, you kind of hear (we’re out) not too long after that.

“Obviously Philly is thinking that we’re losing that game maybe with seven seconds (left), they pull the goalie, they do their thing and Washington scores, so it hurts a lot.”

Newhook opened the scoring 11:32 into the first period. Mailloux sent a stretch pass to Gallagher, who fed Newhook for a one-timer on a 2-on-1.

Seider tied the game with 1:31 left in the period but Montreal retook the lead at 6:17 of the second when Gallagher tapped home a shot from Joel Armia that trickled through Reimer.

Caufield doubled the lead with his 28th at 10:09 and Veleno put Detroit back within one 36 seconds later.

Later in the period, Reimer denied a one-time from Caufield by stretching out for a highlight-reel blocker save, losing his stick in the process, to keep the Red Wings deficit at one.

Mailloux debut

Mailloux was recalled by the Canadiens on Monday night and needed official approval from the NHL to play Tuesday.

The Windsor, Ont. native was fined by Swedish authorities in 2020 after admitting to two charges related to sharing, without her consent, a photo of a woman performing a sexual act.

Montreal, then under general manager Marc Bergevin, was heavily criticized for drafting Mailloux with the 31st pick at the 2021 NHL draft despite the blueliner publicly asking not to be selected.

Worlds bound?

If healthy, Canadiens defenceman Kaiden Guhle said he would represent Canada at the May 10-26 world championship in Czechia.

The 22-year-old from Edmonton missed the season’s final seven games with a head injury, he specified. Guhle finished with 22 points in 70 games.

“That’s the plan,” Guhle said before the game. “It’s always an honour to wear the Maple Leaf and I’ve always thought it was a cool, different scenario the worlds, just giving a chance for guys to play some meaningful games that didn’t really get the chance to.”

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