During the 1942–1943 season, Check was signed by the National Hockey League's Montreal Canadiens, although he continued to play for the Quebec Aces of the Quebec Senior Hockey League through 1944, scoring for them a total of 60 goals and 40 assists. His only NHL game during this period was played with the Detroit Red Wings on March 11, 1944, when the Canadiens provided him as an emergency injury replacement, and he did not score any points. Check did, however, win his first Allan Cup while playing with the Aces, defeating the Port Arthur Shipbuilders in 1944. For the 1944-1945 season, he was loaned to the Chicago Black Hawks, playing 26 games and scoring six goals and two assists.