Don "Dippy" Simmons was a three time Stanley Cup champion as a back up goaltender (to Johnny Bower) with the Toronto Maple Leafs in the 1960s. Previous to that Simmons replaced Terry Sawchuk in Boston and ended up splitting net-tending duties with Harry Lumley with the Bruins of the late 1950. He would finish the late 1960s with the New York Rangers organization, although much of his time was spent in the minor leagues.
Simmons is remembered years after his retirement for two things.
One - he is the answer to a challenging trivia question. Simmons was the second goaltender in NHL history to regularly play with a face mask, after the pioneering Jacques Plante, of course.
Two - he opened up Don Simmons Sports, a very successful "goaltending super store" in Ontario.
In total Simmons played in 249 NHL games over 11 seasons - sporting a 101-101-41 career record. In the playoffs he had a 13-11 record in 24 games, almost all with Boston. He rarely played in the playoffs while backing up Bower in Toronto. But in 1962 he did come off the bench two win two games in the 1962 finals to help secure the Stanley Cup championship.