After a successful season with the Kamloops Blazers of the Western Hockey League, Wilkie was seen as one of the top upcoming defensive prospects for the 1992 NHL Entry Draft and was selected in the 1st round, 20th overall, by the Montreal Canadiens.

The following season, Wilkie returned to the Blazers and made his international debut representing the United States in the 1993 World Junior Ice Hockey Championship (WJC).

The 1996–97 season saw Wilkie make the Montreal Canadiens full-time, appearing in 61 games and scoring 15 points, both NHL career highs.

He has also served as the volunteer assistant coach to the University of Nebraska at Omaha Mavericks, a Division I hockey school.

In 2017, Wilkie was hired as the head coach and general manager of the Omaha Lancers in the United States Hockey League.