Whelan played from 1993 to 2010, most notably for Leeds United, Coventry City, and Middlesbrough.  Whelan started with his home team Leeds United, coming through the youth team. In the 1994-95 season, Whelan finished among the club’s highest scorers. In December 1995, Whelan moved to Coventry City. His goal in a home draw against Southampton was a “Goal of the Month” contender on BBC’s Match of the Day.