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McCrimmon was a right wingers and played for the Prince Albert Raiders of the Saskatchewan Junior Hockey League in 1977-78. He spent the next two seasons with the Wheat Kings. From 1980 to 1984, McCrimmon played for the University of Michigan in the NCAA.
In 1989 McCrimmonn became the general manager of the Wheat Kings - a position he holds to this day. He also took over the coaching position for brief periods from 1990-1992 and from 2004 to 2011.