| Premier Division past winners/runners-up | ||
| Season | Winners | Runners-up |
| 1998/99 | Ramsgate | Deal Town |
| 1999/00 | Deal Town | Thamesmead Town |
| 2000/01 | Chatham Town | Herne Bay |
| 2001/02 | Maidstone United | VCD Athletic |
| 2002/03 | Cray Wanderers | Maidstone United |
| 2003/04 | Cray Wanderers | Thamesmead Town |
| 2004/05 | Ramsgate | Herne Bay |
| 2005/06 | Maidstone United | Beckenham Town |
| 2006/07 | Whitstable Town | VCD Athletic |
| 2007/08 | Thamesmead Town | VCD Athletic |
| 2008/09 | VCD Athletic | Hythe Town |
| 2009/10 | Faversham Town | Herne Bay |
| 2010/11 | Hythe Town | Herne Bay |
| 2011/12 | Herne Bay | Erith & Belvedere |
| 2012/13 | Erith & Belvedere | VCD Athletic |
| 2013/14 | Whyteleafe | Ashford United |
| 2014/15 | Phoenix Sports | Ashford United |