Over his NHL career, Prentice played for the New York Rangers, Boston Bruins, Detroit Red Wings, Pittsburgh Penguins, and Minnesota North Stars.

[1] At the time the Mad Hatters were the New York Rangers' farm team, and Prentice made the jump to the parent club the following season.

[2] On December 27, 1964, in Chicago Stadium, Prentice, while playing for the Bruins, was hauled down on a breakaway by Stan Mikita.

Initially knocked unconscious, Prentice came to and took the awarded penalty shot, scoring on Blackhawks' goaltender Denis DeJordy.

In his first season with Detroit, the Red Wings won the first two games of the 1966 Stanley Cup Finals, before losing four straight.

In 1976, Prentice staged a comeback of sorts, coming out of retirement at 44 years old by suiting up for the Traverse City Bays of the United States Hockey League for 28 games.

His brother, Eric, played five games for the Toronto Maple Leafs during the 1943–44 NHL season.