Conn Smythe was making preparations for his eventual tour of duty in Europe. He felt that Dick Irvin would not be strong enough to deal with player issues while he was gone and Smythe convinced the Montreal Canadiens to hire Irvin. Smythe hired Hap Day as coach.
The Bruins finished 5 points ahead of the Leafs during the regular season. Despite effectively losing league leading scorer Bill Cowley for the playoffs in Game 1, the Bruins prevailed in seven games.
Game 1 at the Boston Garden saw a scoreless first period and the ice broken at 15:33 of the second on a goal by the Bruins Flash Hollett. In the third period, Bobby Bauer was knocked out of the game when his hip was cut by the skate of line mate Milt Schmidt. Bill Cowley was knocked out of the series after a knee on knee collision with Sweeney Schriner. Brimsek held the Leafs off and late goals by Terry Reardon and Eddie Wiseman sealed a 3-0 Bruins win.
Game 2 in Boston was a clean game and saw the Bruins jump out to a 2-0 first period lead on goals by Eddie Wiseman and Milt Schmidt. However, a four goal second period by the Leafs Gordie Drillon, Reg Hamilton and two by Nick Metz put Toronto in a lead they wouldn't relinquish. Third period goals by the Leafs Don Metz and Wiseman's second of the game resulted in a 5-3 Leafs win and tied the series 1-1.
Game 3 at Maple Leaf Gardens saw the Leafs dominate the Bruins in a 7-2 win. Schmidt and Schriner traded goals in the first. Herb Cain put the Bruins up 2-1 at 5:07 of the second after which the Leafs exploded with 3 goals by Syl Apps, Bucko McDonald on the power play and Apps again, on the power play. The Leafs added 3 more in the third by Schriner, Apps completing his Hat trick and Nick Metz. After the game in the Bruins dressing room, Terry Reardon gave a rallying speech that was later heralded in the Boston papers as a major reason for the Bruins' eventual triumph.
Game 4 in Toronto saw Bill Cowley try to return to action with a heavily bandaged knee. But after playing a few shifts, he couldn't continue and didn't play another game in the 1941 playoffs. The game was tie and scoreless heading into the second period until Woody Dumart scored his first of the playoffs. Gordie Drillon responded three minutes later. In the third period, Leafs goalie Turk Broda couldn't control a shot by Herb Cain who slammed home the rebound for a 2-1 Bruins victory, tying the series 2-2.
Game 5 in Boston saw the Leafs Lex Chisholm score the only playoff goal of his career and the Bruins Pat McReavy respond with the first of his. Brimsek and Broda barred the nets, sending the game into overtime. At 17:37 of the first OT, the Leafs Pete Langelle scored the winner. The Leafs had a 3-2 stranglehold on the series.
Game 6 in Toronto saw no goals in the first two periods. Halfway through the third, Drillon put the Leafs up 1-0, who looked posed to take the series. But the Bruins Bobby Bauer responded less than a minute later. Less than two minutes after Bauer's goal, Flash Hollett sent Herb Cain in on Broda who deked him for the game winner. The series was tied 3-3 going back to Boston.
Game 7 in Boston saw the Leafs Bucko McDonald score on a point shot at 13:28. A minute later, the Bruins Flash Hollett tied it up on a similar play. In the second period, the Bruins Jack Crawford high-sticked Pete Langelle, drawing the ire of Leafs GM Conn Smythe, who jumped on the ice and ran after referee Mickey Ion. Crawford received a major penalty, Smythe was fined $100 and was ejected from the game but watched from the stands. With less than six minutes left in the third period, Mel "Sudden Death Hill picked the puck out of a scrum along the boards, skated towards the slot in front of the Leafs net and beat Broda with a shot that went under his arm. The Leafs frantically tried for the tying goal but Brimsek turned aside excellent chances by Apps and Drillon to preserve the 2-1 win and the series victory.