The Leafs and Bruins met for the fourth time in playoffs in the 1930's. The Leafs won the three previous series and would sweep the Bruins, though all three games were decided by one goal with two going into overtime. However, the Bruins would get their revenge the next year when it counted, defeating the Leafs in the 1939 Stanley Cup Finals.
Game 1 was a close checking affair with the only goal scored by George Parsons at 1:31 of the second OT period. Turk Broda posted the shutout.
Game 2 saw the Leafs go 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. Gordie Drillon (last Leaf to lead the league in scoring) quickly responded and the Leafs won 2-1.
Game 3 saw the teams trade goals with Bill Cowley scoring twice in the third period to send the game to overtime. Drillon scored at 10:04 of the first OT to win the series for the Leafs.
Due to a broken toe suffered by goaltender Mike Karakas in the Semi-finals, the Black Hawks would get permission from the Maple Leafs to use goaltender Alfie Moore, who spent the season with the Pittsburgh Hornets of the IAHL in Game 1. 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 would then wrap 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.