A defender), Whiteford began his career with St. Johnstone in 1994 after progressing through the McDiarmid Park youth ranks. In six years as a professional with the Perth club he made seventeen league appearances.
Whiteford went on loan to Stirling Albion during the 1999-2000 season, and he made the move permanent in 2000. In total, he made 30 league appearances for Albion, scoring one goal.
In 2001 he joined Clydebank, for whom he made fourteen appearances in two years.
His most recent club, between 2003 and 2004, was Hamilton Academical. He made seventeen appearances and scored two goals for the Accies.