| KENT SENIOR CUP: THE CUP FINAL MATCHES (includes Kent County Badge finals and seasons’ semi-finalists)
 | 
| Season | Winner | Score | Runner-up | Notes | Date | Venue |  | Beaten semi-finalists(by: Winner / Runner-up) | 
|---|
|  | KENT COUNTY BADGE FINALS | 
| 1885–86 | Chatham United | 3–1 | South Eastern Rangers
 |  | 10 Apr 1886 | Ashford(Victoria Grnd) |  | (bye) / Chatham Victoria
 | 
| 1886–87 | Chatham United | 8–0 | Chatham Victoria |  | 26 Mar 1887 | Chatham (The Lines)
 |  | (bye) / Chatham Standard
 | 
| 1887–88 | Chatham | 0–0 | South Eastern Rangers
 |  | 17 Mar 1888 | Bromley |  | Gravesend  / Folkestone
 | 
| 6–1 | Replay | 31 Mar 1888 | Ashford (Vic) | 
|  | KENT SENIOR CUP FINALS (KENT CUP 1889–1897) | 
| 1888–89 | Chatham | 3–1 | South Eastern Rangers
 |  | 6 Apr 1889 | Chatham |  | Gravesend  / Folkestone
 | 
| 1889–90 | Royal Arsenal | 3–0 | Thanet Wanderers
 |  | 22 Mar 1890 | Chatham |  | Chatham / South Eastern Rangers
 | 
| 1890–91 | Lincoln Regiment
 | 2–1 | South Eastern Rangers
 |  | 11 Apr 1891 | Chatham |  | Chatham  / Royal Arsenal
 | 
| 1891–92 | Highland Light Infantry | 11–0 | Gravesend |  | 12 Mar 1892 | Chatham |  | Chatham  / Ashford United
 | 
| 1892–93 | Ashford United | 2–0 | Chatham |  | 8 Apr 1893 | Chatham |  | West Kent Regiment /  Sheppey United
 | 
| 1893–94 | Royal Ordnance Factories
 | 4–2 | Dartford |  | 7 Apr 1894 | Chatham |  | Folkestone  / New Brompton
 | 
| 1894–95 | Chatham | Cup awarded to the Kent League champions | 
| 1895–96 | Northfleet | 
| 1896–97 | Woolwich Arsenal Reserves
 | 
| 1897–98 | Gravesend United
 | 3–1 | Dartford |  | 2 Apr 1898 | New Brompton |  | Sheppey United  / Chatham
 | 
| 1898–99 | Maidstone United | 1–0 | Folkestone |  | 25 Mar 1899 | Ashford |  | Royal Engineers Utd /  Dartford
 | 
| 1899– 1900
 | Gravesend United
 | 1–1 | Maidstone United |  | 14 Apr 1900 | Tunbridge Wells |  | Dartford  / Folkestone
 | 
| 4–1 | Replay | 30 Apr 1900 | Chatham | 
| 1900–01 | Maidstone United | 3–0 | Cray Wanderers |  | 13 Apr 1901 | Chatham |  | Sheppey United  / Chatham Amateurs
 | 
| 1901–02 | Sittingbourne | 2–2 | Ashford United |  | 31 Mar 1902 | Faversham |  | Swanscombe / Sheppey United
 | 
| 4–1 | Replay | 12 Apr 1902 | Ramsgate | 
| 1902–03 | Maidstone United | 2–1 | Ashford United |  | 13 Apr 1903 | Faversham |  | Sittingbourne  / Eltham
 | 
| 1903–04 | Eltham | 4–1 | Sittingbourne |  | 4 Apr 1904 | Faversham |  | Cray Wanderers  / Dover
 | 
| 1904–05 | Chatham | 3–1 | Sittingbourne |  | 24 Apr 1905 | Faversham |  | Dover  / Eltham
 | 
| 1905–06 | Eltham | 1–0 | Bromley |  | 16 Apr 1906 | Faversham |  | Southern United / Sittingbourne
 | 
| 1906–07 | Maidstone United | 1–0 | Sittingbourne |  | 1 Apr 1907 | Faversham |  | Eltham / Sheppey United
 | 
| 1907–08 | Tunbridge Wells Rangers
 | 1–0 | Sittingbourne |  | 20 Apr 1908 | Maidstone |  | Sheppey United  / Maidstone United
 | 
| 1908–09 | Maidstone United | 4–2 | Northfleet United |  | 12 Apr 1909 | Maidstone |  | Tunbridge Wells Rngrs /  Sittingbourne
 | 
| 1909–10 | Northfleet United | 2–0 | Chatham |  | 28 Mar 1910 | Maidstone |  | Dartford  / Maidstone United
 | 
| 1910–11 | Chatham | 2–1 | Sittingbourne |  | 17 Apr 1911 | Maidstone |  | Sheppey United  / Gravesend United
 | 
| 1911–12 | Catford Southend | 3–0 | Chatham |  | 8 Apr 1912 | Maidstone |  | Bromley  / Sittingbourne
 | 
| 1912–13 | Northfleet United | 2–1 | Gravesend United
 |  | 24 Mar 1913 | Maidstone |  | Tunbridge Wells Rngrs /  Chatham
 | 
| 1913–14 | Maidstone United | 1–0 | Northfleet United |  | 13 Apr 1914 | Maidstone |  | Folkestone  / Chatham
 | 
| 1914–18 | Competition suspended for 4 seasons owing to World War I | 
| 1918–19 | Chatham | 3–0 | Maidstone United | Victory Cup | 21 Apr 1919 | Maidstone |  | Royal Marines (Deal) /Royal Ordnance (W'wich) | 
| 1919–20 | Maidstone United | 2–1 | Northfleet United |  | 5 Apr 1920 | Maidstone |  | Sheppey United  / Sittingbourne
 | 
| 1920–21 | Northfleet United | 1–0 | Ramsgate |  | 28 Mar 1921 | Maidstone |  | Sittingbourne  / Chatham
 | 
| 1921–22 | Maidstone United | 1–0 | Folkestone |  | 17 Apr 1922 | Maidstone |  | Margate Town  / Dartford
 | 
| 1922–23 | Maidstone United | 3–2 | Sittingbourne |  | 2 Apr 1923 | Maidstone |  | Ashford Railway Wks Folkestone
 | 
| 1923–24 | Northfleet United | 1–0 | Dartford |  | 21 Apr 1924 | Maidstone |  | Sittingbourne  / Sheppey United
 | 
| 1924–25 | Northfleet United | 8–2 | Sittingbourne |  | 13 Apr 1925 | Maidstone |  | Grays Thurrock Utd /  Folkestone
 | 
| 1925–26 | Northfleet United | 1–0 | Folkestone |  | 5 Apr 1926 | Maidstone |  | Chatham  / Dartford
 | 
| 1926–27 | Northfleet United | 1–0 | Sheppey United |  | 18 Apr 1927 | Maidstone |  | Chatham  / RN Depot
 | 
| 1927–28 | Northfleet United | 3–1 | Sittingbourne |  | 9 Apr 1928 | Maidstone |  | RN Depot / Cray Wanderers
 | 
| 1928–29 | Sittingbourne | 1–1 | Sheppey United |  | 1 Apr 1929 | Maidstone |  | Chatham  / Folkestone
 | 
| 1–0 | Replay | 3 Apr 1929 | Gillingham | 
| 1929–30 | Sittingbourne | 3–0 | Margate |  | 21 Apr 1930 | Maidstone |  | Northfleet United  / Folkestone
 | 
| 1930–31 | Dartford | 2–2 | Folkestone |  | 6 Apr 1931 | Maidstone |  | Ashford Town  / Tunbridge Wells Rngrs | 
| 5–2 | Replay | 8 Apr 1931 | Maidstone | 
| 1931–32 | Dartford | 2–0 | Sheppey United |  | 28 Mar 1932 | Maidstone |  | Chatham  / Tunbridge Wells Rngrs | 
| 1932–33 | Dartford | 0–0 | Tunbridge Wells Rangers
 |  | 17 Apr 1933 | Maidstone |  | Margate  / Folkestone
 | 
| 2–0 | Replay | 19 Apr 1933 | Northfleet | 
| 1933–34 | Folkestone | 3–0 | Margate |  | 2 Apr 1934 | Maidstone |  | Northfleet United / Ramsgate Press Wndrs
 | 
| 1934–35 | Dartford | 3–2 | Folkestone |  | 22 Apr 1935 | Maidstone |  | Tunbridge Wells Rngrs /  Northfleet United
 | 
| 1935–36 | Margate | 2–1 | Tunbridge Wells Rangers
 |  | 13 Apr 1936 | Maidstone |  | Northfleet United  / Sittingbourne
 | 
| 1936–37 | Margate | 3–2 | Tunbridge Wells Rangers
 |  | 29 Mar 1937 | Maidstone |  | Northfleet United  / Folkestone
 | 
| 1937–38 | Northfleet United | 2–1 | Dover |  | 18 Apr 1938 | Maidstone |  | Margate / Bexley Heath & Welling
 | 
| 1938–39 | Tunbridge Wells Rangers
 | 4–0 | Gillingham |  | 10 Apr 1939 | Maidstone |  | Erith & Belvedere  / Northfleet United
 | 
| 1939–40 | Shorts Sports | 6–1 | Dartford |  | 25 Mar 1940 | Maidstone |  | Canterbury Waverley / Aylesford Paper Mills
 | 
| 1940–41 | Competition suspended owing to World War II | 
| 1941–42 | Erith & Belvedere | 2–1 | Shorts Sports |  | 25 May 1942 | Belvedere |  | Bromley  / Gravesend United
 | 
| 1942–43 | Royal Artillery Depot (Woolwich)
 | 1–0 | Shorts Sports |  | 27 Apr 1943 | Maidstone |  | Gravesend United  / Lloyds
 | 
| 1943–44 | Royal Artillery Depot (Woolwich)
 | 5–3 | Gravesend United
 |  | 10 Apr 1944 | Maidstone |  | Bromley  / Folkestone
 | 
| 1944–45 | Royal Artillery Depot (Woolwich)
 | 5–1 | Lloyds |  | 2 Apr 1945 | Maidstone |  | 12th ITC (Canterbury) /  Gillingham
 | 
| 1945–46 | Gillingham | 5–1 | 12th ITC (Canterbury)
 |  | 22 Apr 1946 | Maidstone |  | Gravesend United  / Erith & Belvedere
 | 
| 1946–47 | Dartford | 3–2 | Bromley |  | 7 Apr 1947 | Maidstone |  | Gillingham  / Folkestone Town
 | 
| 1947–48 | Gillingham | 1–0 | Gravesend & Northfleet
 |  | 29 Mar 1948 | Maidstone |  | Sheppey United  / Bromley
 | 
| 1948–49 | Gravesend & Northfleet
 | 2–2 | Gillingham | After extra time (aet)
 | 18 Apr 1949 | Maidstone |  | Dartford  / Folkestone Town
 | 
| 1–1 | Replay (aet) | 14 May 1949 | Gillingham | 
| 2–0 | 2nd Replay | 31 Aug 1949 | Gillingham | 
| 1949–50 | Bromley | 1–1 | Gillingham |  | 10 Apr 1950 | Maidstone |  | Dover  / Folkestone Town
 | 
| 5–3 | Replay | 19 Apr 1950 | Gillingham | 
| 1950–51 | Snowdown Colliery Welfare
 | 0–0 | Bromley |  | 26 Mar 1951 | Gillingham |  | Sittingbourne  / Dartford
 | 
| 2–1 | Replay (aet) | 19 May 1951 | Gillingham | 
| 1951–52 | Dover | 2–0 | Dartford |  | 14 Apr 1952 | Gillingham |  | Bromley  / Sittingbourne
 | 
| 1952–53 | Gravesend & Northfleet
 | 2–1 | Dartford |  | 6 Apr 1953 | Gillingham |  | Folkestone Town  / Bromley
 | 
| 1953–54 | Canterbury City | 1–0 | Tunbridge Wells United
 |  | 19 Apr 1954 | Gillingham |  | Dover / Gravesend & Northfleet
 | 
| 1954–55 | Tunbridge Wells United
 | 2–1 | Dartford |  | 11 Apr 1955 | Gillingham |  | Tonbridge  / Dover
 | 
| 1955–56 | Snowdown Colliery Welfare
 | 1–1 | Dartford |  | 2 Apr 1956 | Gillingham |  | Ramsgate Athletic  / Canterbury City
 | 
| 2–0 | Replay | 18 Apr 1956 | Gillingham | 
| 1956–57 | Folkestone Town | 2–0 | Tonbridge |  | 22 Apr 1957 | Gillingham |  | Canterbury City  / Tunbridge Wells Utd
 | 
| 1957–58 | Sittingbourne | 1–0 | Ramsgate Athletic
 |  | 07 Apr 1958 | Gillingham |  | Dartford  / Margate
 | 
| 1958–59 | Ashford Town | 2–1 | Tonbridge |  | 30 Mar 1959 | Gillingham |  | Dover  / Snowdown Coll. Welf. | 
| 1959–60 | Dover | 0–0 | Margate |  | 18 Apr 1960 | Maidstone |  | Bromley  / Dartford
 | 
| 1–0 | Replay (aet) | 28 Apr 1960 | Folkestone | 
| 1960–61 | Bexleyheath & Welling
 | 3–0 | Sittingbourne |  | 3 Apr 1961 | Maidstone |  | Cray Wanderers  / Dover
 | 
| 1961–62 | Dover | 1–1 | Ashford Town | 1st Leg | 23 Apr 1962 | Dover |  | Ramsgate Athletic  / Margate
 | 
| 1–1 | 2nd Leg (aet) | 12 May 1962 | Ashford | 
| 2–2 | Aggregate score (after both legs) | 
| 4–1 | Play-off | 20 Aug 1962 | Folkestone | 
| 1962–63 | Ashford Town | 1–0 | Margate |  | 11 May 1963 | Gillingham |  | Tonbridge  / Dartford
 | 
| 1963–64 | Ramsgate Athletic
 | 3–1 | Maidstone United |  | 25 Apr 1964 | Gillingham |  | Bexley United  / Folkestone Town
 | 
| 1964–65 | Tonbridge | 3–0 | Bexley United |  | 19 Apr 1965 | Gillingham |  | Ramsgate Athletic  / Dover
 | 
| 1965–66 | Maidstone United | 1–1 | Ramsgate Athletic
 | 1st Leg | 26 Apr 1966 | Ramsgate |  | Margate  / Dover
 | 
| 3–1 | 2nd Leg | 10 May 1966 | Maidstone | 
| 4–2 | Aggregate score (after both legs) | 
| 1966–67 | Dover | 5–0 | Margate | 1st Leg | 3 Apr 1967 | Margate |  | Dartford  / Ramsgate Athletic
 | 
| 1–0 | 2nd Leg | 6 Apr 1967 | Dover | 
| 6–0 | Aggregate score (after both legs) | 
| 1967–68 | Dover | 1–2 | Bexley United | 1st Leg | 24 Apr 1968 | Bexley |  | Tonbridge / Gravesend & Northfleet
 | 
| 3–0 | 2nd Leg (aet) | 8 May 1968 | Dover | 
| 4–2 | Aggregate score (after both legs) | 
| 1968–69 | Folkestone | 4–0 | Margate | 1st Leg | 30 Apr 1969 | Folkestone |  | Herne Bay  / Bexley United
 | 
| 0–2 | 2nd Leg | 8 May 1969 | Margate | 
| 4–2 | Aggregate score (after both legs) | 
| 1969–70 | Dartford | 1–0 | Margate | 1st Leg | 4 May 1970 | Margate |  | Erith & Belvedere  / Folkestone
 | 
| 4–1 | 2nd Leg | 9 May 1970 | Dartford | 
| 5–1 | Aggregate score (after both legs) | 
| 1970–71 | Dover | 1–0 | Dartford | 1st Leg | 19 Apr 1971 | Dover |  | Ashford Town  / Sheppey United
 | 
| 2–2 | 2nd Leg | 28 Apr 1971 | Dartford | 
| 3–2 | Aggregate score (after both legs) | 
| 1971–72 | Dover | 2–0 | Dartford | 1st Leg | 5 Apr 1972 | Dover |  | Canterbury City  / Sheppey United
 | 
| 1–2 | 2nd Leg | 13 Apr 1972 | Dartford | 
| 3–2 | Aggregate score (after both legs) | 
| 1972–73 | Dartford | 6–2 | Folkestone | 1st Leg | 26 Mar 1973 | Dartford |  | Canterbury City  / Maidstone United
 | 
| 4–2 | 2nd Leg | 4 Apr 1973 | Folkestone | 
| 10–4 | Aggregate score (after both legs) | 
| 1973–74 | Margate | 2–0 | Maidstone United |  | 13 Apr 1974 | Maidstone |  | Canterbury City  / Bexley United
 | 
| 1974–75 | Tonbridge | 2–1 | Maidstone United |  | 5 Apr 1975 | Maidstone |  | Dartford  / Ashford Town
 | 
| 1975–76 | Maidstone United | 1–0 | Canterbury City | After extra time (aet)
 | 30 Apr 1976 | Maidstone |  | Margate  / Bexley United
 | 
| 1976–77 | Bromley | 1–0 | Gravesend & Northfleet
 |  | 30 Apr 1977 | Maidstone |  | Ashford Town  / Dartford
 | 
| 1977–78 | Folkestone and Shepway
 | 1–0 | Maidstone United |  | 15 Apr 1978 | Maidstone |  | Sheppey United / Gravesend & Northfleet
 | 
| 1978–79 | Maidstone United | 2–1 | Dartford | After extra time (aet)
 | 16 Apr 1979 | Maidstone |  | Gravesend & Northfleet /  Sheppey United
 | 
| 1979–80 | Maidstone United | 1–0 | Dartford |  | 7 Apr 1980 | Maidstone |  | Bromley  / Dover
 | 
| 1980–81 | Gravesend & Northfleet
 | 2–0 | Ashford Town |  | 20 Apr 1981 | Maidstone |  | Maidstone United  / Dover
 | 
| 1981–82 | Maidstone United | 3–0 | Ashford Town |  | 12 Apr 1982 | Gillingham |  | Tonbridge Angels  / Gravesend & Northfleet | 
| 1982–83 | Folkestone | 4–0 | Dover |  | 2 May 1983 | Gillingham |  | Bromley  / Maidstone United
 | 
| 1983–84 | Fisher Athletic | 1–0 | Maidstone United |  | 7 May 1984 | Gillingham |  | Folkestone  / Ashford Town
 | 
| 1984–85 | Folkestone | 4–2 | Welling United |  | 6 May 1985 | Gillingham |  | Thanet United  / Fisher Athletic
 | 
| 1985–86 | Welling United | 2–0 | Dover Athletic |  | 5 May 1986 | Gillingham |  | Gravesend & Northfleet /  Dartford
 | 
| 1986–87 | Dartford | 2–0 | Maidstone United |  | 4 May 1987 | Gillingham |  | Ashford Town  / Fisher Athletic
 | 
| 1987–88 | Dartford | 1–0 | Maidstone United |  | 3 May 1988 | Gillingham |  | Welling United  / Bromley
 | 
| 1988–89 | Maidstone United | 1–0 | Welling United | After extra time (aet)
 | 1 May 1989 | Gillingham |  | Dartford / Gravesend & Northfleet
 | 
| 1989–90 | Maidstone United | 1–0 | Gillingham |  | 7 May 1990 | Gillingham |  | Dover Athletic  / Dartford
 | 
| 1990–91 | Dover Athletic | 1–0 | Gravesend & Northfleet
 |  | 6 May 1991 | Gillingham |  | Gillingham  / Maidstone United
 | 
| 1991–92 | Bromley | 3–1 | Hythe Town | After extra time (aet)
 | 4 May 1992 | Gillingham |  | Dartford  / Ashford Town
 | 
| 1992–93 | Ashford Town | 3–2 | Bromley |  | 3 May 1993 | Gillingham |  | Gravesend & Northfleet Welling United
 | 
| 1993–94 | Margate | 2–1 | Dover Athletic |  | 2 May 1994 | Gillingham |  | Charlton Athletic  / Welling United
 | 
| 1994–95 | Charlton Athletic | 4–2 | Gillingham | After extra time (aet)
 | 8 May 1995 | Gillingham |  | Tonbridge Angels  / Fisher
 | 
| 1995–96 | Ashford Town | 3–0 | Charlton Athletic |  | 6 May 1996 | Sittingbourne |  | Gillingham  / Fisher
 | 
| 1996–97 | Bromley | 4–1 | Dover Athletic |  | 5 May 1997 | Millwall |  | Gillingham  / Fisher Athletic
 | 
| 1997–98 | Margate | 1–0 | Gravesend & Northfleet
 |  | 4 May 1998 | Northfleet |  | Gillingham  / Dover Athletic
 | 
| 1998–99 | Welling United | 1–0 | Folkestone Invicta
 |  | 3 May 1999 | Folkestone |  | Margate  / Fisher Athletic
 | 
| 1999– 2000
 | Gravesend & Northfleet
 | 3–0 | Folkestone Invicta
 |  | 1 May 2000 | Northfleet |  | Dartford  / Dover Athletic
 | 
| 2000–01 | Gravesend & Northfleet
 | 4–0 | Dover Athletic |  | 7 May 2001 | Dover |  | Folkestone Invicta  / Bromley
 | 
| 2001–02 | Gravesend & Northfleet
 | 5–0 | Margate |  | 6 May 2002 | Margate |  | Fisher Athletic  / Ashford Town
 | 
| 2002–03 | Margate | 2–1 | Welling United | After extra time (aet)
 | 30 Apr 2003 | Welling |  | Erith & Belvedere  / Bromley
 | 
| 2003–04 | Margate | 2–1 | Folkestone Invicta
 |  | 28 Apr 2004 | Folkestone |  | Dover Athletic  / Bromley
 | 
| 2004–05 | Margate | 2–1 | Dover Athletic |  | 2 May 2005 | Folkestone |  | Folkestone Invicta / Gravesend & Northfleet
 | 
| 2005–06 | Bromley | 3–2 | Gravesend & Northfleet
 | After extra time (aet)
 | 27 Apr 2006 | Bromley |  | Ramsgate  / Margate
 | 
| 2006–07 | Bromley | 3–1 | Tonbridge Angels |  | 24 Apr 2007 | Bromley |  | Ashford Town  / Maidstone United
 | 
| 2007–08 | Ebbsfleet United | 4–0 | Cray Wanderers |  | 26 Jul 2008 | Bromley |  | Margate  / Bromley
 | 
| 2008–09 | Welling United | 6–1 | Whitstable Town |  | 16 Apr 2009 | Welling |  | Ramsgate  / Bromley
 | 
| 2009–10 | Sittingbourne | 3–1 | Folkestone Invicta
 |  | 4 May 2010 | Folkestone |  | Cray Wanderers  / Welling United
 | 
| 2010–11 | Dartford | 4–1 | Bromley |  | 2 May 2011 | Dartford |  | Ramsgate  / Cray Wanderers
 | 
| 2011–12 | Hythe Town | 1–0 | Dartford |  | 24 Apr 2012 | Dartford |  | Dover Athletic  / Charlton Athletic
 | 
| 2012–13 | Charlton Athletic | 7–1 | Tonbridge Angels |  | 1 May 2013 | Tonbridge |  | Thamesmead  / Ebbsfleet United
 | 
| 2013–14 | Ebbsfleet United | 4–0 | Dover Athletic |  | 5 May 2014 | Gillingham |  | Whitstable Town  / Bromley
 | 
| 2014–15 | Charlton Athletic | 1–0 | Gillingham |  | 30 Apr 2015 | Gillingham |  | Ramsgate  / Margate
 | 
| 2015–16 | Dartford | 3–1 | Charlton Athletic |  | 26 Apr 2016 | Dartford |  | Greenwich Borough /  Ebbsfleet United
 | 
| 2016–17 | Dover Athletic | 2–0 | Welling United |  | 1 May 2017 | Maidstone |  | Folkestone Invicta  / Charlton Athletic
 | 
| 2017–18 | Maidstone United | 0–0 | Folkestone Invicta
 |  | 24 Apr 2018 | Maidstone |  | Bromley  / Charlton Athletic
 | 
| 4–2 | Penalty shots | 
| 2018–19 | Maidstone United | 1–1 | Bromley |  | 16 Apr 2019 | Bromley |  | Gillingham  / Tonbridge Angels
 | 
| 3–2 | Penalty shots | 
| 2019–20 | Dartford | 6–1 | Whitstable Town | Final Delayed
 | 24 Nov 2021 | Dartford |  | Phoenix Sports  / Gillingham
 | 
| 2020–21 | Competition suspended owing to the COVID-19 pandemic | 
| 2021–22 | Dartford | 6–2 | Folkestone Invicta
 |  | 17 May 2022 | Chatham |  | Welling United  / Hythe Town
 | 
| 2022–23 | Margate | 1–1 | Chatham Town |  | 3 May 2023 | Gillingham |  | Ramsgate  / Welling United
 | 
| 5–4 | Penalty shots | 
| 2023–24 | Maidstone United | 4–0 | Ebbsfleet United |  | 17 Apr 2024 | Bromley |  | Dartford  / Chatham Town
 | 
| 2024–25 | Welling United | 1–0 | Ebbsfleet United |  | 2 Apr 2025 | Gillingham |  | Dover Athletic  / Tonbridge Angels
 |