The Blackhawks took down the Canadiens 4-3 after a shootout, bringing an unfortunate end to Canadiens rookie Ivan Demidov's huge debut.
With the loss, Montreal (89) is now just four points ahead of the Columbus Blue Jackets (85) for the second Wild Card spot.
Should Montreal lose out in regulation time the rest of the way, and Columbus wins their final two games, the Canadiens will ultimately choke their way out of what should've been an open-and-shut case for their spot in the playoffs.
Juraj Slafkovský (18) scored the game-tying goal for the Canadiens after the Blackhawks went up 3-2 with three straight goals.
But after failing to score even once in the shootout, Chicago's Frank Nazar put one home for the win.
Red Wings 6-4 Stars
Despite being knocked out of playoff contention, the Red Wings pulled off a late rally after scoring four goals in the third period.
Lucas Raymond (one goal, two assists) and Moritz Seider (one goal, two assists) both put up three points each in the third period.
Dallas' final game of the regular season will be against the Nashville Predators on Wednesday while the Red Wings will play in back-to-back games to wrap up their season against the New Jersey Devils (Wednesday) and Toronto Maple Leafs (Thursday).
Around the league
Clayton Keller (29) scored twice en route to the Utah Hockey Club's 7-3 win over the Nashville Predators. Utah has one game left (vs. St. Louis Blues) before their season officially ends while Nashville will take on the Stars in their final game.
The New York Rangers scored four straight unanswered goals to take down the Florida Panthers 5-3. Next up on the Rangers' schedule to close out their season is a matchup against the Tampa Bay Lightning on Thursday - the same team that the Panthers will face on Tuesday.
*Note: current live matchups include - Edmonton Oilers vs. Los Angeles Kings and Vancouver Canucks vs. San Jose Sharks.