Kingston, Ontario native Dick Cherry was born on February 28th, 1937. He played his junior hockey with the Barrie Flyers, joining the Boston Bruins during his second year in Barrie. Cherry played six games on the Bruins blue line in 1956-57 without recording a point.
The next four seasons were spent primarily in the American Hockey League without another NHL opportunity. In 1961, Cherry joined the Kingston Frontenacs of the Eastern Professional Hockey League. After scoring 60 points in 53 games in his second season in Kingston, Cherry retired and taught high school.
After two years in the classroom, Dick Cherry returned to the ice with the Kingston Aces, then the next year he spent with the Oklahoma City Blazers before leaving the game in 1967. When the Philadelphia Flyers joined the NHL in the 1967 NHL Expansion Draft they claimed Cherry from the Bruins and with a solid opportunity to be a regular, Cherry returned to the game.
In 1968-69, Cherry played 71 games for the Philadelphia Flyers scoring nine goals and 15 assists. The next year, he posted seven points in 68 games, but by the 1970-71 season he was out of the NHL.
Cherry returned to the Oklahoma City Blazers then spent two more years Kingston Aces before retiring again. Dick Cherry made his third and final comeback in 1974 playing his final season with the Napanee Comets.