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