The Derbyshire FA Centenary Cup was an annual friendly association football competition, primarily played between Derbyshire's two professional clubs, Derby County and Chesterfield.

The first ever tie was a two-legged affair between Derbyshire's two Football League clubs, Derby County and Chesterfield, to earn the 'County Title'.

The 1996–97 match broke the established timetable and was held in November.

After several years of sending their reserve team to fulfil the fixture, Derby County declined to enter the 2003 competition and were replaced by non-league Alfreton Town, who beat Chesterfield 2–0.

Matches follow typical friendly competition rules, with a draw being decided on penalties.