MONTREAL (AP) 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.

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

The Red Wings prevailed in a dramatic 5-4 overtime victory over the Canadiens on home ice a day earlier.

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 Dylan 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 with a shot from behind the net that banked off Primeau’s pads and into the net.

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.

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