The Jets scored four times in the final 2 minutes and 8 seconds of regulation before Dylan Samberg completed the comeback in overtime, ending Winnipeg's nine-game losing streak.
Elsewhere, the Columbus Blue Jackets stunned the Colorado Avalanche 7-2, while the Utah Mammoth defeated the Toronto Maple Leafs 3-2 in another impressive result.
Winnipeg Jets 5-4 Montreal Canadiens (OT)
Winnipeg delivered an extraordinary comeback at the Bell Centre after trailing Montreal 4-0 early in the third period.
Owen Beck opened the scoring for the Canadiens before Josh Anderson doubled their advantage. Cole Caufield then scored twice, including a power-play goal early in the third period, to put Montreal firmly in control.
However, the Jets refused to surrender.
Tyrel Bauer started the comeback with his first NHL goal with 2 minutes and 39 seconds remaining. Morgan Barron followed with another goal before Kyle Connor scored twice, including the equaliser with just 32 seconds left on the clock.
Dylan Samberg then completed the turnaround 3 minutes and 30 seconds into overtime, giving Winnipeg a memorable victory.
The result ended the Jets' nine-game losing streak and represented the latest four-goal comeback victory in NHL history.
Columbus Blue Jackets 7-2 Colorado Avalanche
The Blue Jackets delivered one of the night's biggest surprises by overwhelming the Avalanche 7-2 at Nationwide Arena.
Charlie Coyle led the way with two goals and two assists, matching his career high with four points.
Mathieu Olivier also contributed a goal and two assists, while Valeri Nichushkin and Cole Sillinger each recorded a goal and an assist.
Columbus scored four times in the second period to take control of the contest, ending Colorado's three-game winning streak.
Cale Makar and Nazem Kadri scored for the Avalanche, but their efforts were not enough to prevent a heavy defeat.
Utah Mammoth 3-2 Toronto Maple Leafs
Utah secured an important victory over Toronto in a closely contested encounter.
Jack Roslovic scored twice for the Mammoth, while Nick Schmaltz delivered the decisive goal after receiving an assist from Clayton Keller.
The result highlighted Utah's growing confidence against established NHL opponents and provided another boost to their 2026/27 campaign.
Other NHL results
The Minnesota Wild defeated the Philadelphia Flyers 4-2, with Danila Yurov scoring an empty-net goal late in the third period to seal the victory.
The Tampa Bay Lightning overcame the Detroit Red Wings 4-2 after building an early three-goal advantage. Brayden Point scored twice, with Nikita Kucherov assisting on both goals.
The New York Rangers defeated the St. Louis Blues 3-1, with Adam Fox, Oliver Bjorkstrand and Eeli Tolvanen finding the net.
The Vegas Golden Knights edged the Pittsburgh Penguins 3-2, with Trevor Connelly and Tomas Hertl scoring important third-period goals.
The Dallas Stars survived a late Washington Capitals fightback to win 6-5. Jason Robertson scored a natural hat-trick as Dallas established a four-goal advantage before holding on for victory.
The New Jersey Devils defeated the Edmonton Oilers 4-3 in a shootout. Jack Hughes scored twice and added an assist, while goaltender Connor Hellebuyck helped New Jersey secure the victory.
The Nashville Predators produced an impressive 4-1 victory over the Carolina Hurricanes, with Filip Forsberg, Roman Josi and Ross Colton leading the way.
Winnipeg's remarkable comeback steals the spotlight
Although several teams recorded important victories, Winnipeg's comeback against Montreal was undoubtedly the standout story of the night.
Scoring four goals in the closing minutes after trailing by four was an extraordinary achievement, particularly for a team that had lost nine consecutive games.
The victory could provide the Jets with the confidence needed to revive their season, while Montreal will be left disappointed after surrendering a seemingly unassailable advantage.