Verified record · 84 season records
League Cup winners since 1923
The knockout thread of the record: winners from 1923–24 to 2018–19, runners-up where the roll records them, and the silences — wartime and 1959 to 1968 — kept as the source states them.
| Season | Winner | Runner-up |
|---|---|---|
| 1923–24 | Northfleet Utd | not recorded |
| 1924–25 | Dartford | not recorded |
| 1925–26 | Sittingbourne | not recorded |
| 1926–27 | Royal Naval Depot | not recorded |
| 1927–28 | Sittingbourne Paper Mill | not recorded |
| 1928–29 | Folkestone Reserves | not recorded |
| 1929–30 | Folkestone Reserves | not recorded |
| 1930–31 | Gillingham Reserves | not recorded |
| 1931–32 | Northfleet Utd | not recorded |
| 1932–33 | Tunbridge Wells | not recorded |
| 1933–34 | Tunbridge Wells | not recorded |
| 1934–35 | Northfleet Utd | not recorded |
| 1935–36 | Margate Reserves | not recorded |
| 1936–37 | Northfleet Utd | not recorded |
| 1937–38 | Northfleet Utd | not recorded |
| 1938–39 | Ashford Town | not recorded |
| 1939–40 | Shorts Sports | not recorded |
| 1943–44 | Lloyds FC | not recorded |
| 1944–45 | Snowdown Col. Welfare | not recorded |
| 1945–46 | Gillingham Reserves | not recorded |
| 1946–47 | Folkestone | not recorded |
| 1947–48 | Margate | not recorded |
| 1948–49 | Ramsgate Athletic | not recorded |
| 1949–50 | Canterbury City | not recorded |
| 1950–51 | Snowdown Col. Welfare | not recorded |
| 1951–52 | Folkestone | not recorded |
| 1952–53 | Tunbridge Wells | not recorded |
| 1953–54 | Margate | not recorded |
| 1954–55 | Tunbridge Wells | not recorded |
| 1955–56 | Gillingham Reserves | not recorded |
| 1956–57 | Dover | not recorded |
| 1957–58 | Deal Town | not recorded |
| 1958–59 | Sittingbourne | not recorded |
| 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 |
| 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 |
The gaps, as the source states them
- No competition 1940 – 1943
- No Comp 1959 – 1968
- 2019/20 – Abandoned Competition
- 2020/21 – No Competition
The roll continues after the league champions record ends in 2013; why the two spans differ is discussed in the league history.
Finals between neighbouring towns are picked out — as labelled interpretation — on the Kent derbies page.