- “Fellowship of Freedom” 🏆 presented by Councillor J. G. B. Stone. (In use: 1927 – 2011)
| Year | Team | |
| 2025 | TBD!! | |
| 2024 | Littlebourne Rec | |
| 2023 | Castle 'A' (Oare) | |
| 2022 | Gentil Knyght 'C' | |
| 2021 | COVID | |
| 2020 | COVID | |
| 2019 | Alma 'A' (Painters Forstal) | |
| 2018 | Two Brothers | |
| 2017 | Smugglers (Herne) | |
| 2016 | Dover Castle (Teynham) | |
| 2015 | Gentil Knyght 'C' | |
| 2014 | Golden Lion (Broad Oak) | |
| 2013 | Dove Inn 'B' (Dargate) | |
| 2012 | Market Inn 'B' (Faversham) | |
| 2011 | Red Lion 'A' (Stodmarsh) | |
| 2010 | Compasses (Crundale) | |
| 2009 | Four Horseshoes (Whitstable) | |
| 2008 | Artichoke 'A' (Chartham) | |
| 2007 | White Hart (Canterbury) | |
| 2006 | Huntsman & Horn (Broomfield) | |
| 2005 | Kestrels | |
| 2004 | Two Brothers | |
| 2003 | Way Out Inn (Westmarsh) | |
| 2002 | Market Inn 'A' (Faversham) | |
| 2001 | Castle (Oare) | |
| 2000 | Three Tuns (Faversham) | |
| 1999 | Queens Head (Boughton) | |
| 1998 | Huntsman & Horn (Broomfield) | |
| 1997 | NOT PLAYED / UNKNOWN | |
| 1996 | NOT PLAYED / UNKNOWN | |
| 1995 | NOT PLAYED / UNKNOWN | |
| 1994 | Ravens | |
| 1993 | Artichoke (Chartham) | |
| 1992 | Castle 'A' (Oare) | |
| 1991 | Post Office | |
| 1990 | NOT PLAYED / UNKNOWN | |
| 1989 | Sturry Road 'B' (Canterbury) | |
| 1988 | Market Inn 'B' (Faversham) | |
| 1987 | Oddfellows 'A' (Canterbury) | |
| 1986 | Jolly Sailor (Whitstable) | |
| 1985 | Woodmans Hall 'C' (Boughton) | |
| 1984 | Three Mariners (Oare) | |
| 1983 | Market Inn 'A' (Faversham) | |
| 1982 | Brewers Delight 'C' | |
| 1981 | NOT PLAYED / UNKNOWN | |
| 1980 | Golden Lion 'A' (Broad Oak) | |
| 1979 | Anchor (Wingham) | |
| 1978 | Bretts Sports (Chartham) | |
| 1977 | All Knights | |
| 1976 | NOT PLAYED / UNKNOWN | |
| 1975 | Bretts Sports (Chartham) | |
| 1974 | Kings Head 'A' (Chartham) | |
| 1973 | Brewers Delight 'B' | |
| 1972 | Market Inn 'A' (Faversham) | |
| 1971 | Woodmans Hall 'A' (Boughton) | |
| 1970 | Dolphin 'B' | |
| 1969 | Greyhound (Aylesham) | |
| 1968 | Golden Lion 'A' (Broad Oak) | |
| 1967 | Maidens Head (Wincheap) | |
| 1966 | Brewers Delight | |
| 1965 | Mermaid (Bishopsbourne) | |
| 1964 | Chantry Social Club (Longport) | |
| 1963 | Dolphin 'B' | |
| 1962 | NOT PLAYED / UNKNOWN | |
| 1961 | Dolphin 'A' | |
| 1960 | Gate Inn (Marshside) | |
| 1959 | British Legion | |
| 1958 | Brewers Delight | |
| 1957 | Rising Sun (Sturry Road) | |
| 1956 | Mill House (Canterbury) | |
| 1955 | White Hart (Canterbury) | |
| 1954 | British Legion | |
| 1953 | Maidens Head (Wincheap) | |
| 1952 | British Legion | |
| 1951 | Two Brothers | |
| 1950 | Golden Lion (Broad Oak) | |
| 1949 | Post Office Telephones | |
| 1948 | Maidens Head (Wincheap) | |
| 1947 | Old City of Canterbury | |
| 1946 | Coopers Sports | |
| 1945 | WWII | |
| 1944 | WWII | |
| 1943 | WWII | |
| 1942 | WWII | |
| 1941 | WWII | |
| 1940 | WWII | |
| 1939 | Municipal Workers Guild | |
| 1938 | Bigglestons Sports | |
| 1937 | Brewers Delight | |
| 1936 | Gas & Water Social Club | |
| 1935 | Past & Present Buffs | |
| 1934 | Terriers | |
| 1933 | Municipal Workers Guild | |
| 1932 | O.P.I.E. (G.P.O.) | |
| 1931 | City of Canterbury | |
| 1930 | White Hart (Canterbury) | |
| 1929 | Risers (Rising Sun, Sturry Road) | |
| 1928 | Brewers Delight | |
| 1927 | Halfway House | |