| Premier Division Cup |
| Season |
Winners |
Runners-up |
| 1998/99 |
Deal Town |
VCD Athletic |
| 1999/00 |
VCD Athletic |
Faversham Town |
| 2000/01 |
Ramsgate |
Greenwich Borough |
| 2001/02 |
Maidstone United |
Whitstable Town |
| 2002/03 |
Cray Wanderers |
VCD Athletic |
| 2003/04 |
Thamesmead Town |
Cray Wanderers |
| 2004/05 |
Ramsgate |
Herne Bay |
| 2005/06 |
Maidstone United |
VCD Atheltic |
| 2006/07 |
Thamesmead Town |
Whitstable Town |
| 2007/08 |
Erith Town |
Hythe Town |
| 2008/09 |
Croydon |
Erith Town |
| 2009/10 |
Herne Bay |
Sevenoaks Town |
| 2010/11 |
Herne Bay |
Hythe Town |
| 2011/12 |
VCD Athletic |
Corinthian |
| 2012/13 |
Erith & Belvedere |
Corinthian |
| 2013/14 |
Beckenham Town |
Corinthian |
| 2014/15 |
Greenwich Borough |
Tunbridge Wells |
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