He played junior hockey for the Flin Flon Bombers from 1956-58, winning the Memorial Cup in 1956-57. Prior to 1967, Rupp played occasionally in the NHL with the New York Rangers and the Toronto Maple Leafs but mostly in the minor pros. In 1967-68 he got his big break and became a regular with the Leafs. After playing the 1973-74 season with the Hershey Bears of the American Hockey League (AHL), Rupp played for two seasons with the Vancouver Blazers/Calgary Cowboys in the World Hockey Association before concluding his career in 1977 with the Rochester Americans of the AHL.
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