Winnipeg recovered after blowing 3-0 and 4-3 leads.
Connor, who finished with three points, was in the slot when he took the pass and buried a shot past Canadiens goalie Carey Price exactly three minutes into overtime to the disappointment of the Bell Centre crowd.
Price played his 557th game for the Canadiens, which surpassed the legendary Jacques Plante for the most by a goalie in franchise history. He stopped 27 shots in the loss.
Mason, who had played just one game in nearly three months, made 36 saves as the Jets reached the 50-win mark for the first time in franchise history.
Paul Byron pulled Montreal within 3-2 at the 3:19 mark of the third period by pouncing on a rebound for his 20th goal on the season, and then Kerby Rychel deflected a point shot at 10:15 of the third period to make it a 3-3 game. It was Rychel's first goal of the season.
Winnipeg regained the lead just 24 seconds later when Sami Niku netted a goal in his NHL debut, on his first career shot on goal, but again the Habs drew even when Alex Galchenyuk potted a power-play goal with 1:42 remaining in regulation.
Patrik Laine's 44th goal of the season on the power play opened the scoring at the 12:25 mark of the first period. Laine fired a one-timer from just beyond the left circle for his 20th man-advantage marker of the campaign, tops in the NHL.
Nikolaj Ehlers doubled the Winnipeg lead with his 29th of the season at 14:19 by finishing a give-and-go passing play with Paul Stastny.
Jack Roslovic made it a 3-0 game with a goal very similar to Laine's at 15:58 of the second period, but the Canadiens roared back.
Artturi Lehkonen was on the spot for a loose puck in the slot and whipped a shot past Mason with 59.3 seconds remaining in the middle frame to put the hosts on the board.
--Field Level Media
Winnipeg | Montreal | |
Kyle Connor 3 | Points | Alex Galchenyuk 2 |
Kyle Connor 1 | Goals | Alex Galchenyuk 1 |
Kyle Connor 2 | Assists | Jeff Petry 2 |
Patrik Laine 1 | Power Play Goals | Alex Galchenyuk 1 |
N/A | Short Handed Goals | N/A |
Steve Mason .900 | Save Percentage | Carey Price .844 |
Steve Mason 36 | Saves | Carey Price 27 |
Team | Shots | Goals | Power Play | Penalty Kill | Penalty Mins | Face Offs Won |
Winnipeg | 32 | 5 | 1-2 | 4-5 | 24 | 24 |
Montreal | 40 | 4 | 1-5 | 1-2 | 8 | 35 |