| League Cup Winners 1923/24 - 1958/59 | |
| Season | 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 comp 1940 - 1943 | |
| 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 | |
| Stats supplied by Doug Smith HBFC | |