1938–39 Toronto Maple Leafs season

The 1938–39 Toronto Maple Leafs season was Toronto's 22nd season of operation in the National Hockey League (NHL). The Maple Leafs again advanced to the Stanley Cup Finals, losing to the Boston Bruins.

Playoffs
The Maple Leafs finished in third place in the regular season, which matched them up against the New York Americans in the first round, best of three series. After sweeping the Americans in 2 games, the Leafs played the Detroit Red Wings in the next round in another best of three series, which they won 2–1. In the finals, they played the Boston Bruins, who defeated them 4–1.

Regular season

 * Scoring
 * Goaltending

Playoffs

 * Scoring
 * Goaltending

Transactions

 * October 12, 1938: Traded Charlie Conacher to the Detroit Red Wings for $16,000
 * November 3, 1938: Acquired Gus Marker from the Montreal Maroons for $4,000
 * November 15, 1938: Acquired Norman Mann from the New York Rangers for $4,000
 * December 8, 1938: Acquired Doc Romnes from the Chicago Black Hawks for Bill Thoms
 * December 19, 1938: Acquired Bucko McDonald from the Detroit Red Wings for Bill Thomson and $10,000

Farm teams

 * Syracuse Stars