| First Division past winners/runners-up | ||
| Season | Winners | Runners-up |
| 1968/69 | Brett Sports | Tunbridge Wells |
| 1969/70 | Faversham Town | Kent Police |
| 1970/71 | Faversham Town | Chatham Town |
| 1971/72 | Chatham Town | Brett Sports |
| 1972/73 | Sheppy United | Sittingbourne |
| 1973/74 | Chatham Town | Sittingbourne |
| 1974/75 | Sheppy United | Medway |
| 1975/76 | Sittingbourne | Dartford Amateurs |
| 1976/77 | Medway | Sittingbourne |
| 1977/78 | Faversham Town | Sheppy United |
| 1978/79 | Sheppy United | Hythe Town |
| 1979/80 | Chatham Town | Cray Wanderers |
| 1980/81 | Cray Wanderers | Chatham Town |
| 1981/82 | Erith & Belvedere | Sittingbourne |
| 1982/83 | Crockenhill | Hythe Town |
| 1983/84 | Sittingbourne | Sheppy United |
| 1984/85 | Tunbridge Wells | Hythe Town |
| 1985/86 | Alma Swanley | Sittingbourne |
| 1986/87 | Greenwich Borough | Crockenhill |
| 1987/88 | Greenwich Borough | Faversham Town |
| 1988/89 | Hythe Town | Deal Town |
| 1989/90 | Faversham Town | Sittingbourne |
| 1990/91 | Sittingbourne | Cray Wanderers |
| 1991/92 | Herne Bay | Faversham Town |
| 1992/93 | Tonbridge AFC | Herne Bay |
| 1993/94 | Herne Bay | Furnace |
| 1994/95 | Sheppy United | Chatham Town |
| 1995/96 | Furness | Dartford |
| 1996/97 | Herne Bay | Ramsgate |
| 1997/98 | Herne Bay | Folkestone Invicta |