| Reserves Division(s) League Cup | ||
| Season | Winners | Runners-up |
| 1978/79 | Dover Athletic | Darenth Heathside |
| 1979/80 | ChathamTown | Deal Town |
| 1980/81 | Sittingbourne | Chatham Town |
| 1981/82 | Maidstone United | Dover Athletic |
| 1982/83 | Erith & Belvedere | Hythe Town |
| 1983/84 | Erith & Belvedere | Darenth Heathside |
| 1984/85 | Sheppy United | Fisher Athletic |
| 1985/86 | Faversham Town | Deal Town |
| 1986/87 | Sittingbourne | Ashford Town |
| 1987/88 | Sittingbourne | Sheppy United |
| 1988/89 | Hythe Town | Folkestone Invicta |
| 1989/90 | Canterbury City | Dover Athletic |
| 1990/91 | Fisher Athletic | Beckenham Town |
| 1991/92 | Folkestone Invicta | Whitstable Town |
| 1992/93 | Tonbridge AFC | Canterbury City |
| 1993/94 | Dover Athletic | Tonbridge AFC |
| 1994/95 | Thamesmead Town | Chatham Town |
| 1995/96 | Folkestone Invicta | Dover Athletic |
| 1996/97 | Hastings Town | Deal Town |
| 1997/98 | Thamesmead Town | Herne Bay |
| 1998/99 | Dover Athletic | Deal Town |
| 1999/00 | Thamesmead Town | Deal Town |
| 2000/01 | Margate | Folkestone Invicta |
| 2001/02 | Dover Athletic | Thamesmead Town |
| 2002/03 | Cray Wanderers | Dover Athletic |
| 2003/04 | Cray Wanderers | Maidstone United |
| 2004/05 | Beckenham Town | Bromley |
| 2005/06 | Dartford | Whitstable Town |
| 2006/07 | Thamesmead Town | Deal Town |
| 2007/08 | Ashford Town | Dartford |
| 2008/09 | Thamesmead Town | Whitstable Town |
| 2009/10 | Dartford | VCD Athletic |
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