The 1938–39 Boston Bruins season was the Bruins' 15th season in the NHL, and they were coming off of a very successful regular season in 1937–38, winning the American Division with a record of 30–11–7, however, they lost to the Toronto Maple Leafs in the Stanley Cup semi-finals. This season, the Bruins would meet the Maple Leafs in a rematch, and win the series 4–1 to win the Stanley Cup for the second time, and the first time in 10 years.