He retired from playing professional ice hockey in 1947. Roberts for many years held the distinction of being both the youngest and the oldest goaltender in National Hockey League history. On December 8, 1925, he made his debut at age 19 for the Boston Bruins which made him the youngest goaltender in NHL history (the record was later broken by Harry Lumley 20 years later). On November 25, 1951, Roberts (at that point an assistant trainer with the Chicago Black Hawks) had to play the third period of the game because Lumley had been injured. Even though Roberts did not give up a goal, the Hawks still lost to the Detroit Red Wings, 5-2. Roberts at age 45, in his last NHL game, became the oldest player ever to play in an NHL game (the record was later broken by Gordie Howe and then Chris Chelios). He is still the oldest goaltender to play in an NHL game and was also the final NHL player to have been active in the 1920s.