The Maple Leafs and Bruins met for the fourth time in playoffs in the 1930's. The Leafs won the three previous series but the Bruins were heavy favorites, having won the season series convincingly. Turk Broda and Tiny Thompson played every minute in goal. Toronto effectively checked the Kraut Line, keeping them off the scoresheet in the series.
Game 1 at Maple Leaf Gardens was a close checking, rough affair and scoreless through regulation. The Bruins killed off a penalty to Ray Getliffe in the first overtime period. In the second OT, in front of Toronto's net, Milt Schmidt missed a pass which sprang Nick Metz and rookie George Parsons on a 2 on 1. Metz's pass to Parsons was perfect and he fired a shot over Thompson's pad at 1:31 for the game winner.
Game 2 at Toronto had the Bruins vowing to not match the Leafs defensive style and to forecheck more. Good to their word, the Bruins pressed hard and 70% of the game was spent in Toronto's zone. After a scoreless first period, the turning point came when league scoring champion Gordie Drillon, who was being effectively shadowed by Ray Getliffe, kicked Getliffe in the skate, cutting his foot deeply and knocking him out of the game. The Leafs went in front 1-0 on a second period goal by "Pep" Kelly until Charlie Sands tied it up at 7:37 of the third period. Ex-Leaf Art Jackson was assigned to cover Drillon but wasn't up to the task as Drillon scored and the Leafs won 2-1. The Leafs Conn Smythe acknowledged his club was lucky to come out ahead, praised the many rushes made by Eddie Shore and indicated the Bruins lack of finishing off chances was their downfall. Smythe had attendants at each corner of the rink with sticks, so if a Leaf broke his, he wouldn't have to skate back to the bench for a replacement.
Game 3 at Boston Garden saw several line-up changes. Ray Getliffe played but Mel Hill was recalled from the minors and spelled him off. Robert "Red" Hamill and Frank Brimsek were also recalled but not used. Toronto was without Busher Jackson who suffered torn hand ligaments. In a repeat of Game 2, the Bruins held a wide edge in chances while the Leafs played defensive hockey and waited for breaks. Drillon opened the scoring in the second period before Bill Cowley (playing with a broken nose) tied it up early in the third. Pep Kelly and Cowley traded goals and late in the period, Jack Portland, who'd played an outstanding defensive game for the Bruins, missed an open net. Drillon scored on a 50 foot screen shot at 10:04 of the first OT to win the series for the Leafs. Hockey columnists noted that the underdogs won every series.
Due to a broken toe suffered by goaltender Mike Karakas in the Semi-finals, the Black Hawks got permission from the Maple Leafs to use goaltender Alfie Moore in Game 1. Moore spent the season with the Maple Leafs farm team the Pittsburgh Hornets of the IAHL. He responded by helping the Black Hawks win the game 3–1.
Moore was declared ineligible by NHL President Frank Calder for Game 2 and as Karakas was still unavailable, Chicago called up Paul Goodman from the Wichita Skyhawks of the AHA. The Maple Leafs would even up the series with a 5–1 victory. The Black Hawks would get Karakas back into the lineup for Game 3 (wearing a steel-toed skate to protect his broken toe), and he helped the Hawks to a 2–1 victory.
Chicago wrapped up the series in Game 4, winning by a score of 4–1 to earn its 2nd Stanley Cup in team history, shocking the hockey world. So improbable was the Black Hawks' victory that NHL President Frank Calder didn't arrange for the Stanley Cup to be sent to Chicago for Game 4, having it remain in Toronto, resulting in no presentation ceremony after Chicago's win.