- “Kentish Gazette Challenge 🏆” presented by Mr G. R. Hews of Kent County Newspapers.
| Year | Team | |
| 2025 | TBD!! | |
| 2024 | Market Inn 'B' (Faversham) | |
| 2023 | Chislet Club | |
| 2022 | Kestrels | |
| 2021 | COVID | |
| 2020 | COVID | |
| 2019 | Red Lion (Dunkirk) | |
| 2018 | Evenhill Crusaders 'B' (Littlebourne) | |
| 2017 | Faversham Town F.C. | |
| 2016 | Smugglers 'B' (Herne) | |
| 2015 | Dover Castle (Teynham) | |
| 2014 | Frog & Orange (Shatterling) | |
| 2013 | Imperial (Canterbury) | |
| 2012 | Golden Lion (Broad Oak) | |
| 2011 | Plough 'A' (Lewson Street) | |
| 2010 | Market Inn 'B' (Faversham) | |
| 2009 | Castle 'B' (Oare) | |
| 2008 | Royal Oak (Broad Oak) | |
| 2007 | Share & Coulter (Greenhill) | |
| 2006 | Bunn Penny 'B' (Herne Bay) | |
| 2005 | Huntsman & Horn (Broomfield) | |
| 2004 | Gentil Knyght 'B' | |
| 2003 | Anchor (Wingham) | |
| 2002 | Mill House (Canterbury) | |
| 2001 | Heron 'A' (Herne Bay) | |
| 2000 | Tannington Social Club (Canterbury) | |
| 1999 | Two Brewers (Whitstable) | |
| 1998 | Three Tuns (Faversham) | |
| 1997 | Three Mariners (Oare) | |
| 1996 | Half Moon & Seven Stars (Preston) | |
| 1995 | Dolphin 'A' (Canterbury) | |
| 1994 | Alma (Painters Forstal) | |
| 1993 | Three Mariners (Oare) | |
| 1992 | Brewers Delight | |
| 1991 | Castle (Oare) | |
| 1990 | Artichoke (Chartham) | |
| 1989 | Golden Lion 'A' (Broad Oak) | |
| 1988 | Sturry Road 'B' (Canterbury) | |
| 1987 | Kestrels | |
| 1986 | Swan Inn 'A' (Sturry) | |
| 1985 | Market Inn 'B' (Faversham) | |
| 1984 | Monument | |
| 1983 | Globetrappers | |
| 1982 | Three Mariners (Oare) | |
| 1981 | Aylesham Social Club (Aylesham) | |
| 1980 | Gentil Knyght 'A' | |
| 1979 | Dolphin 'B' (Canterbury) | |
| 1978 | Brewers Delight 'C' | |
| 1977 | Anchor (Wingham) | |
| 1976 | University 'A' | |
| 1975 | Old City 'A' | |
| 1974 | Gentil Knyght 'B' | |
| 1973 | Kings Head 'A' (Chartham) | |
| 1972 | Market Inn 'B' (Faversham) | |
| 1971 | Ship Inn 'A' (Upstreet) | |
| 1970 | Golden Lion 'B' (Broad Oak) | |
| 1969 | Dolphin 'B' (Canterbury) | |
| 1968 | Greyhound 'A' (Aylesham) | |
| 1967 | Golden Lion 'A' (Broad Oak) | |
| 1966 | Dolphin 'C' (Canterbury) | |
| 1965 | Godfrey Sports 'A' | |
| 1964 | Gentil Knyght | |
| 1963 | Gas & Water Sports | |
| 1962 | Dolphin 'B' (Canterbury) | |
| 1961 | Special Constables | |
| 1960 | East Kent 'A' | |
| 1959 | Mermaid (Bishopsbourne) | |
| 1958 | Kings Head (Chartham) | |
| 1957 | Brewers Delight | |
| 1956 | Rising Sun (Sturry Road) | |
| 1955 | Kings Head (Chartham) | |
| 1954 | Sportsmans Arms (Barham) | |
| 1953 | Dolphin 'B' (Canterbury) | |
| 1952 | Mill House (Canterbury) | |
| 1951 | George & Dragon (Fordwich) | |
| 1950 | Kings Head (Chartham) | |
| 1949 | White Hart (Canterbury) | |
| 1948 | Post Office Telephones | |
| 1947 | Unicorn 'B' | |
| 1946 | Forresters Sports | |
| 1945 | WWII | |
| 1944 | WWII | |
| 1943 | WWII | |
| 1942 | WWII | |
| 1941 | WWII | |
| 1940 | WWII | |
| 1939 | East Kent Sports | |
| 1938 | Wilshiers Sports | |
| 1937 | Courts Sports | |
| 1936 | Post Office Sports | |
| 1935 | British Legion | |
| 1934 | Westbere Social | |