He won the Stanley Cup in 1933 with the New York Rangers against the Toronto Maple Leafs three games to one on April 13, 1933.

For the 1930 season, Dillon was called up to the National Hockey League by the New York Rangers, with whom he would stay until 1939, never missing a single game during his time with the team.

[3][4] Dillon was selected as one of the games' stars for his work in holding the Primeau-Conacher-Jackson "Kid Line" to no goals in the final.

After the Red Wings, Dillon played another two years in the American Hockey League (AHL) before retiring altogether.

He was married to Bessie Marion Dillion (née Brooks) with whom he had four sons: Keith, William (Bill), Caroll and Garry Matthew Dillon, born on September 25, 1937.