1938 – 39 Boston Bruins season 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 . Regular season . In the off - season , the NHL would lose a franchise , as the Montreal Maroons would fold , leaving the league with seven teams , and eliminating the American and Canadian Division format the league had been using since 1926 . The Bruins would make a key acquisition , acquiring Roy Conacher from the Kirkland Lake Hargreaves of the NOHA . Boston would see goaltender Tiny Thompson get injured during an early season game , forcing the club to sign Frank Brimsek , who played for the Providence Reds of the IAHL . Brimsek stepped in and played great hockey , and when Thompson came back from his injury , the Bruins decided to deal him to the Detroit Red Wings for Norm Smith . Brimsek would help lead the Bruins to 1st place in the NHL standings , as they finished the season with a record of 36 – 10 – 2 , earning 74 points , their highest point total since the 1929 – 30 season . Bill Cowley would lead the team with 42 points , despite missing 14 games due to injuries . His 34 assists were a league high . Rookie Roy Conacher scored an NHL high 26 goals , and added 11 assists to finish with 37 points . Milt Schmidt continued to show improvement , scoring a career high 32 points . Flash Hollett led the Bruins defense with 27 points , as he scored 10 goals and added 17 assists , while Dit Clapper scored 13 goals and 26 points from the blueline . In goal , rookie Frank Brimsek led the NHL with 33 wins and a 1 . 56 GAA , earning both the Vezina Trophy and the Calder Trophy . He also recorded 10 shutouts , which was among the league leaders . Playoffs . In the playoffs , Boston would have a 1st round bye , advancing straight to the NHL semi - finals , where they would face the 2nd place New York Rangers in a best of 7 series . New York had 58 points during the regular season , which was 16 less than the Bruins . The series opened at Madison Square Garden in New York , and the Bruins would win a thrilling , triple overtime game by a score of 2 – 1 . Game 2 moved to the Boston Garden , and Boston took a 2 – 0 series lead with a 3 – 2 overtime victory . The Bruins took a commanding 3 – 0 lead in the series with a 4 – 1 win , looking to close out the series in the 4th game , as the series shifted back to New York . The Rangers would hold off elimination , defeating Boston 2 – 1 , and then in game 5 in Boston , the game would be decided in overtime , with New York once again winning by a 2 – 1 score to cut the series lead to 3 – 2 . Game 6 was played back in New York , and the Rangers easily defeated the Bruins 3 – 1 , to tie the series up at 3 games , forcing a 7th game to be played in Boston . The game would be tied 1 – 1 after regulation time , and would not be settled until the 3rd overtime period , when Boston finally snapped the tie , winning the game 2 – 1 , and taking the series 4 – 3 , to advance to the Stanley Cup finals . The Bruins opponent was the Toronto Maple Leafs , who finished the season with a 19 – 20 – 9 record , earning 47 points , which was 27 points fewer than Boston . The Leafs defeated the New York Americans and Detroit Red Wings to earn a spot in the best of seven finals . The series would begin with 2 games in Boston , and each team won a game , as the series moved to Maple Leaf Gardens for games three and four . Boston would take control in Toronto , winning game three by a 3 – 1 score , then shutting out the Leafs 2 – 0 in game four , to take a 3 – 1 series lead . Boston then returned home for game five , and defeated Toronto 3 – 1 , to win their first Stanley Cup in 10 years , and second in team history .