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Ted McCaskill began his trek to professional hockey playing two years with the Kitchener Canucks in the mid 1950s before playing with his hometown Kapuskasing Huskies of the NOHA for two seasons. He then made a surprise move, picking up and playing in Britain for two years, first with the Edinburgh Royals and also the Paisley Pirates, where he averaged a goal per game in each season.
Upon his return to Canada, McCaskill again played for Kapuskasing for two seasons in the NOHA. In 1962-63 he began a five-year association with the Nashville Dixie Flyers of the EHL. In 1964-65 he had his best year as a pro, scoring 60 goals and 125 points in 72 games. With NHL expansion in 1967-68 McCaskill was signed as a free agent by the Minnesota North Stars and played four games with them, picking up two assists.
The balance of his year was spent with the North Stars' minor league affiliate in Memphis. Although he never had another shot at the NHL, McCaskill continued to play professional hockey for another seven years, including a season-and-a-half in the WHA with the Los Angeles Sharks. He closed down his career after playing with the Binghamton Dusters of the NAHL in 1974-75