Hill started playing for the Boston Bruins of the National Hockey League in 1937–38, and played only six games, scoring two goals. The next season, he scored ten goals and had twenty points, but it was in the playoffs that year that he rose into prominence. In the semi-finals that year against the New York Rangers, he scored three sudden-death overtime goals to help the Bruins knock off the Rangers and go on to win the Stanley Cup. All in all, he had six goals and nine points in twelve games in the playoffs that year.