The Capital Counties Cup was founded as a tournament for clubs in the South-East of England (intially those in feeder leagues linked to the Isthmian League) who either were unable to enter the F.A. Vase or declined to enter.
The competition has always been a straight knock-out, with no seedings or exemptions.
| Season | Winner | Runner-up | Result | In FCHD |
| 1999-2000 | Tring Athletic | Bedmond Sports & Social | 1-1, 3-1 on pens | None |
| 2000-01 | Tring Athletic | Virginia Water | 1-0 | None |
| 2001-02 | Enfield Town | Pitstone & Ivinghoe | 3-1 | None |
| 2002-03 | White Ensign | Tring Athletic | 1-0 | None |
| 2003-04 | Frenford Senior | Manford Way | 2-1 | None |
| 2004-05 | Winslow United | White Ensign | 4-1 | None |
| 2005-06 | White Ensign | Manford Way | 1-0 | None |
| 2006-07 | White Ensign | Hatfield Town | 4-1 | None |
| 2007-08 | None |