He played junior hockey for the Kitchener Canucks from 1954 to 1956 and then played two seasons for the senior Kapuskasing Huskies in his hometown. In 1958 McCaskill went to Great Britain and played one season each for the Edinburgh Royals and the Paisley Pirates. In 1960 he returned home and played two seasons for the senior Kapuskasing GM's. He returned to playing with the Binghamton Dusters in 1974-75 and then retired. McCaskill coached the Mohawk Valley Comets in 1975-76 and the Long Beach Sharks in 1977-78. He scored 13 goals and 13 assists in 91 WHA games.