Kent League Cup History
Competition History
Past Winners
| 1958-59 | Sittingbourne |
| 1957-58 | Deal Town |
| 1956-57 | Dover |
| 1955-56 | Gillingham Reserves |
| 1954-55 | Tunbridge Wells United |
| 1953-54 | Margate |
| 1952-53 | Tunbridge Wells United |
| 1951-52 | Folkestone Town |
| 1950-51 | Snowdown CW |
| 1949-50 | Canterbury City |
| 1948-49 | Ramsgate Athletic |
| 1947-48 | Margate |
| 1946-47 | Folkestone Town |
| 1945-46 | Gillingham Reserves |
| 1944-45 | Snowdown CW |
| 1943-44 | Lloyds |
| 1939-40 | Shorts Sports |
| 1938-39 | Ashford Town |
| 1937-38 | Northfleet United |
| 1936-37 | Northfleet United |
| 1935-36 | Margate Reserves |
| 1934-35 | Northfleet United |
| 1933-34 | Tunbridge Wells United |
| 1932-33 | Tunbridge Wells United |
| 1931-32 | Northfleet United |
| 1930-31 | Gillingham Reserves |
| 1929-30 | Folkestone Reserves |
| 1928-29 | Folkestone Reserves |
| 1927-28 | Sittingbourne Paper Mill |
| 1926-27 | R.N. Depot |
| 1925-26 | Sittingbourne |
| 1924-25 | Dartford |
| 1923-24 | Northfleet United |