League Cup Winners since 1923

Winners
1923/24 Northfleet Utd
1924/25 Dartford
1925/26 Sittingbourne
1926/27 Royal Naval Depot
1927/28 Sittingbourne Paper Mill
1928/29 Folkestone Reserves
1929/30 Folkestone Reserves
1930/31 Gillingham Reserves
1931/32 Northfleet Utd
1932/33 Tunbridge Wells
1933/34 Tunbridge Wells
1934/35 Northfleet Utd
1935/36 Margate Reserves
1936/37 Northfleet Utd
1937/38 Northfleet Utd
1938/39 Ashford Town
1939/40 Shorts Sports
No competition 1940 – 1943

Winners

1943/44 Lloyds FC
1944/45 Snowdown Col. Welfare
1945/46 Gillingham Reserves
1946/47 Folkestone
1947/48 Margate
1948/49 Ramsgate Athletic
1949/50 Canterbury City
1950/51 Snowdown Col. Welfare
1951/52 Folkestone
1952/53 Tunbridge Wells
1953/54 Margate
1954/55 Tunbridge Wells
1955/56 Gillingham Reserves
1956/57 Dover
1957/58 Deal Town
1958/59 Sittingbourne

No Comp 1959 – 1968

Season – Winners – Runners-up
1968/69 – Margate – Brett Sports
1969/70 – Kent Police – Chatham
1970/71 – Faversham – Hastings Utd
1971/72 – Chatham – Ashford United
1972/73 – Folkestone – Sittingbourne
1973/74 – Sittingbourne – Chatham
1974/75 – Tunbridge Wells – Sittingbourne
1975/76 – Sheppey Utd – Sittingbourne
1976/77 – Medway – Dartford Gtworth
1977/78 – Tunbridge Wells – Sheppy Utd
1978/79 – Sheppey 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 – Sheppey 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 – Sheppey Utd
1996/97 – Herne Bay – Sheppey Utd
1997/98 – Greenwich Borough – Herne Bay

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
2015/16 – Hollands & Blair – Erith & Belvedere
2016/17 – Ashford United – Cray Valley PM
2017/18 – Whitstable Town – Tunbridge Wells
2018/19 – Chatham Town – Corinthian
2019/20 – Abandoned Competition
2020/21 – No Competition