| Year | Team | |
| 2025 | TBD!! | |
| 2024 | Ratling Club (Aylesham) | |
| 2023 | Chislet Club 'A' (Hersden) | |
| 2022 | Chislet Club (Hersden) | |
| 2021 | COVID | |
| 2020 | COVID | |
| 2019 | ISG Red Lion (Dunkirk) | |
| 2018 | Huntsman & Horn (Broomfield) | |
| 2017 | Evenhill Crusaders 'B' (Littlebourne) | |
| 2016 | Kestrels | |
| 2015 | Evenhill Crusaders (Littlebourne) | |
| 2014 | Red Lion 'B' (Dunkirk) | |
| 2013 | Dover Castle (Teynham) | |
| 2012 | Faversham Town F.C. | |
| 2011 | Golden Lion (Broad Oak) | |
| 2010 | St. Stephen's Sports Club | |
| 2009 | The Plough (Lewson Street) | |
| 2008 | Market Inn 'B' (Faversham) | |
| 2007 | Catholic Club (Herne Bay) | |
| 2006 | Share & Coulter (Greenhill) | |
| 2005 | Smugglers (Herne) | |
| 2004 | White Hart (Canterbury) | |
| 2003 | Four Horsehoes 'B' (Whitstable) | |
| 2002 | Red Lion 'A' (Dunkirk) | |
| 2001 | Kestrels | |
| 2000 | Sturry Road 'B' (Canterbury) | |
| 1999 | Thannington Sports Club (Canterbury) | |
| 1998 | Imperial 'B' (Canterbury) | |
| 1997 | Kestrels | |
| 1996 | Queen's Head (Boughton) | |
| 1995 | Prince of Wales (Hoath) | |
| 1994 | Royal Oak (Chartham Hatch) | |
| 1993 | Polo Farm | |
| 1992 | Dolphin 'A' (Canterbury) | |
| 1991 | Golden Lion 'B' (Broad Oak) | |
| 1990 | Castle (Oare) | |
| 1989 | Artichoke 'B' (Chartham) | |
| 1988 | Littlebourne Rec | |
| 1987 | Kings Head 'A' (Wincheap) | |
| 1986 | Kestrels | |
| 1985 | Woodmans Hall 'B' (Boughton) | |
| 1984 | St. Stephen's Sports Club | |
| 1983 | Halfmoon & Seven Stars (Preston) | |
| 1982 | Bretts Sports 'B' | |
| 1981 | Taverners | |
| 1980 | Royal Oak 'B' (Chartham Hatch) | |
| 1979 | Royal Oak 'A' (Chartham Hatch) | |
| 1978 | Chequers 'A' | |
| 1977 | Globetrappers | |
| 1976 | NOT PLAYED / UNKNOWN | |
| 1975 | Post Office Sports | |
| 1974 | Gentil Knyght 'C' | |
| 1973 | Old City of Canterbury | |
| 1972 | Pilgrims | |
| 1971 | Gentil Knyght 'B' | |
| 1970 | Cross Keys 'B' (Chartham) | |
| 1969 | Brewers Delight 'B' | |
| 1968 | Dolphin 'B' (Canterbury) | |
| 1967 | Artichoke (Chartham) | |
| 1966 | Golden Lion (Broad Oak) | |
| 1965 | Rose & Crown (Selling) | |
| 1964 | Godfrey Sports 'A' | |
| 1963 | Artichoke (Chartham) | |
| 1962 | Gas & Waters Sports Club | |
| 1961 | Dolphin 'B' (Canterbury) | |
| 1960 | Special Constables | |
| 1959 | Mill House 'B' (Canterbury) | |
| 1958 | Mermaid (Bishopsbourne) | |
| 1957 | Royal Air Forces Association | |
| 1956 | Brewers Delight | |
| 1955 | Beverlie | |
| 1954 | EKR Carsports 'B' | |
| 1953 | EKR Carsports 'C' | |
| 1952 | Falstaff Tap (Canterbury) | |
| 1951 | EKR Carsports 'B' | |
| 1950 | Bretts Social Club | |
| 1949 | British Legion 'B' | |
| 1948 | EKR Carsports 'A' | |
| 1947 | NOT USED | |
| 1946 | NOT USED | |
| 1945 | WWII | |
| 1944 | WWII | |
| 1943 | WWII | |
| 1942 | WWII | |
| 1941 | WWII | |
| 1940 | WWII | |
| 1939 | Falstaff Tap (Canterbury) | |
| 1938 | Brewers Delight 'B' | |
