Career
Fleming began his career in 1993 with Meadowbank Thistle, where he made a total of 49 appearances before moving to Dunfermline Athletic in 1994. He has also played for Dundee, Livingston, Partick Thistle and Hamilton Academical. In the 2006–2007 season with Hamilton injury restricted him to only 19 first team appearances.
He signed for Alloa Athletic under freedom of contract as manager Allan Maitland built a new squad for the 2007-2008 season.
He was released in May 2008. Flea also broke his leg in the process.
Derek is now a player/coach for Linlithgow Rose.