Winnipeg native Clifford “Cliff” Pennington began his career as an ice hockey forward in the Manitoba Junior Hockey League in 1955, playing two seasons with the St. Boniface Canadiens and winning the league’s championship Turnbull Cup in 1956. He then joined the Flin Flon Bombers of the Saskatchewan Junior Hockey League in 1957 where he stayed, at least nominally, until 1960. He had intermittent runs with the Winnipeg Warriors of the Western Hockey League during this period, but his break came in 1959 when he signed with the Kitchener-Waterloo Dutchmen of the Senior Ontario Hockey League, despite also being on the roster for the Bombers. Although he spent most of the season with the Dutchmen, he also did plenty of travelling. Most notably, he accompanied them to the 1960 Winter Olympics as they represented Canada in ice hockey and took home a silver medal. At the tournament he played in four matches, but did not score any goals. Back in Canada he suited up for two more matches with the Warriors and played for the Bombers and the Edmonton Oil Kings in the playoffs for the Memorial Cup, Canada’s annually trophy for the junior men’s ice hockey champions.
Pennington turned professional in 1960, playing at first for the Hull-Ottawa Canadiens of the Eastern Professional Hockey League, with whom he won the league championship, MVP award (shared with Fred Burchell), and Rookie of the Year honor. He also signed a contract to join the Montreal Canadiens of the National Hockey League. He played in only four matches, scoring one goal, with Montreal prior to being traded to the Boston Bruins in June 1961. The 1961-1962 season was his only full one in the NHL and he split the following year between the Bruins and the Kingston Frontenacs of the EPHL (and winning his second league championship). In June 1963 he was traded to the San Francisco Seals of the World Hockey League but, after 26 games, he was traded back to Boston in December and ended up spending the remainder of the season with the Quebec Aces of the American Hockey League. His career became only less stable after that; from 1964 until his 1974 retirement from active play he suited up with the Verdun Pirates of the Quebec Senior Hockey League (1964-1965), the Los Angeles Blades of the WHL (1965-1966), the Florida Rockets (1966-1967), Nashville Dixie Flyers (1967-1969), Jacksonville Rockets (1971-1972), and St. Petersburg/Suncoat Suns (1971-1974) of the Eastern Hockey League and the Des Moines Oak Leafs (1969-1971) and Flint Generals (1970-1971) of the International Hockey League. His most notable award during this period was the James Gatschene Trophy as IHL league MVP in 1970. He is a member of the Manitoba Hockey Hall of Fame.
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