| Year | Winner[1] | Final Result | Runner-up | Venue of final |
|---|
| 1888 | Woolston Works | 2–0 | Winchester | County Ground, Southampton |
| 1889 | Royal Engineers,Aldershot | 5–1 | Portsmouth FA | County Ground, Southampton |
| 1890 | Royal Engineers,Aldershot | 3–2 | King's Royal Rifles | County Ground, Southampton |
| 1891 | St. Mary's | 3–1 | Royal Engineers,Aldershot | County Ground, Southampton |
| 1892 | St. Mary's | 5–0 | Army Medical Staff, Netley | County Ground, Southampton |
| 1893 | Freemantle | 2–1 | St. Mary's | County Ground, Southampton |
| 1894 | Royal Engineers,Aldershot | 1–0 | St. Mary's | County Ground, Southampton |
| 1895 | Southampton St. Mary's | 5–0 | Royal Artillery, Fareham | County Ground, Southampton |
| 1896 | Royal Artillery, Portsmouth | 3–1 | Southampton St. Mary's | County Ground, Southampton |
| 1897 | Cowes | 1–1 | 2nd Gordon Highlanders (Aldershot) | County Ground, Southampton |
| Cowes | 2–1 | 2nd Gordon Highlanders (Aldershot) | County Ground, Southampton |
| 1898 | Eastleigh Athletic | 2–1 | 2nd Gordon Highlanders (Aldershot) | County Ground, Southampton |
| 1899 | Southampton Reserves | 2–2 | Ryde | United Services Ground, Portsmouth |
| Southampton Reserves | 2–0 | Ryde | Portsmouth (Uncertain Ground) |
| 1900 | Ryde | 1–0 | Portsmouth Reserves | United Services Ground, Portsmouth |
| 1901 | Southampton Reserves | 2–0 | Ryde | Fratton Park, Portsmouth |
| 1902 | Southampton Reserves | 2–0 | Ryde | Fratton Park, Portsmouth |
| 1903 | Portsmouth Reserves | 0–0 | Southampton Reserves | Freemantle Football Ground, Southampton |
| Portsmouth Reserves | 1–0 | Southampton Reserves | Freemantle Football Ground, Southampton |
| 1904 | Ryde Sports | 1–0 | Portsmouth Reserves | The Dell, Southampton |
| 1905 | Southampton Reserves | 2–0 | Portsmouth Reserves | The Dell, Southampton |
| 1906 | Cowes | 5–1 | HMS Excellent, Portsmouth | The Dell, Southampton |
| 1907 | Southampton Reserves | 1–1 | 2nd Batt. Grenadier Guards | Fratton Park, Portsmouth |
| Southampton Reserves | 1–1 | 2nd Batt. Grenadier Guards | Fratton Park, Portsmouth |
| 2nd Batt. Grenadier Guards andSouthampton (joint holders) |
| 1908 | Southampton Reserves | 1–0 | RMLI (Gosport) | Fratton Park, Portsmouth |
| 1909 | Eastleigh Athletic | 2–0 | 2nd Cameron Highlanders (Tidworth) | The Dell, Southampton |
| 1910 | Southampton Reserves | 5–2 | Royal Army Medical Corps (Aldershot) | Fratton Park, Portsmouth |
| 1911 | Eastleigh Athletic | 4–2 | Kings Royal Rifles Corps (Gosport) | Fratton Park, Portsmouth |
| 1912 | Cowes | 1–1 | Southampton Reserves | Fratton Park, Portsmouth |
| Cowes | 1–0 | Southampton Reserves | Fratton Park, Portsmouth |
| 1913 | Portsmouth Reserves | 4–1 | Bournemouth | The Dell, Southampton |
| 1914 | Southampton Reserves | 4–0 | Royal Engineers | Dean Court, Bournemouth |
| 1915–1919 | No Competition owing to war |
| 1920 | Southampton Reserves | | | |
| 1921 | Southampton Reserves | | Thornycroft Athletic | |
| 1922 | RMLI (Gosport) | | Bournemouth | |
| 1923 | Sholing Athletic | 4–2 | Thornycrofts (Woolston) | The Dell, Southampton |
| 1924 | Bournemouth & Boscombe Athletic | | | |
| 1925 | RAMC (Aldershot) | 4–2 | Cowes | The Dell, Southampton |
| 1926 | Cowes | 3–1 | Ryde Sports | The Dell, Southampton |
| 1927 | Ryde Sports | | Cowes | The Dell, Southampton |
| 1928 | Aldershot | | | |
| 1929 | RAOC (Hilsea) | | | The Dell, Southampton |
| 1930 | Cowes | 3–0 | Royal Marines | The Dell, Southampton |
| 1931 | Winchester City | 4–2 | Andover | The Dell, Southampton |
| 1932 | Newport | 2–1[10] | Cowes | The Dell, Southampton |
| 1933 | Newport | 3–2 | Andover | The Dell, Southampton |
| 1934 | Cowes | | RASC Training Centre (Aldershot) | The Dell, Southampton |
| 1935 | Southampton 'A' | | Bournemouth & Boscombe Athletic | The Dell, Southampton |
| 1936 | RASC Training Centre (Aldershot) | | Ryde Sports | The Dell, Southampton |
| RASC Training Centre (Aldershot) | | Ryde Sports | The Dell, Southampton |
| RASC Training Centre (Aldershot) | | Ryde Sports | The Dell, Southampton |
| RASC Training Centre (Aldershot) &Ryde Sports (joint holders) |
| 1937 | Ryde Sports | | 2nd Kings Own Royal Regiment | The Dell, Southampton |
| 1938 | RASC Training Centre (Aldershot) | | Southampton 'A' | The Dell, Southampton |
| 1939 | Ryde Sports | | Portsmouth Gas Company | The Dell, Southampton |
| 1940 | Southampton Res | | | |
| 1941 | Folland Aircraft | | Royal Marines, Portsmouth | Fratton Park, Portsmouth |
| 1942 | Southampton Police | 3–1 | Folland Aircraft | |
| 1943 | 3 Batt Royal Marines, Southampton | | Cunliffe Owen FC | The Dell, Southampton |
| 1944 | Southampton Police | 1–0 | Royal Marines, Eastney | Fratton Park, Portsmouth |
| 1945 | Southampton Police | | | |
| 1946 | Cowes | 2–1 aet | Bournemouth Gasworks | The Dell, Southampton |
| 1947 | RAOC (Hilsea) | | | |
| 1948 | Cowes | 2–1 aet | RAMC, Aldershot | The Dell, Southampton |
| 1949 | Andover | 2–1 | Romsey Town | The Dell, Southampton |
| 1950 | Southampton 'A' | 4–1 | Cowes | The Dell, Southampton |
| 1951 | Andover | 4–1 | Newport | The Dell, Southampton |
| 1952 | Portsmouth 'A' | | RAMC, Crookham | The Dell, Southampton |
| 1953 | Bournemouth Gasworks | 4–3 | Newport | The Dell, Southampton |
| 1954 | Bournemouth Gasworks | 2–1 | Cowes | The Dell, Southampton |
| 1955 | Newport | 2–0 | Southampton 'A' | The Dell, Southampton |
| 1956 | Andover | 4–3 | Cowes Sports | The Dell, Southampton |
| 1957 | Fareham Town | 2–0 | Andover | The Dell, Southampton |
| 1958 | Alton Town | | Cowes Sports | |
| 1959 | Bournemouth & Boscombe 'A' | 1–0 aet | Portsmouth 'A' | Dean Court, Bournemouth |
| 1960 | RAMC (Crookham) | | Fareham Town | The Dell, Southampton |
| 1961 | Newport | | | |
| 1962 | Salisbury | | Fareham Town | The Dell, Southampton |
| 1963 | Fareham Town | | | |
| 1964 | Salisbury | 3–0 | Aldershot | The Dell, Southampton |
| 1965 | Andover | 8–0 | Basingstoke Town | The Dell, Southampton |
| 1966 | Newport | 3–2 aet | Alton Town | Fratton Park, Portsmouth |
| 1967 | Cowes | 2–1 | Newport | Partlands, Ryde |
| 1968 | Fareham Town | 2–1 | Hawker-Siddeley | Fratton Park, Portsmouth |
| 1969 | Alton Town | 2–1 | Pirelli General | Walled Meadow, Andover |
| 1970 | Waterlooville | 3–1 | Gosport Borough | Fratton Park, Portsmouth |
| 1971 | Basingstoke Town | 3–2 replay after 1-1 draw | Fareham Town | Fratton Park, Portsmouth |
| 1972 | Alton Town | 1–0[11] | Brockenhurst | |
| 1973 | Waterlooville | | Newport | The Dell, Southampton |
| 1974 | Sholing Sports | 2–1 | Waterlooville | The Dell, Southampton |
| 1975 | Farnborough Town | 5–1 aet | Basingstoke Town | |
| 1976 | Southampton 'A' | 2–0 | Waterlooville | The Dell, Southampton |
| 1977 | Pirelli General | 1–0 | Farnborough Town | Recreation Ground (Aldershot) |
| 1978 | Alton Town | | Pirelli General | The Dell, Southampton |
| 1979 | Romsey Town | 1–0 | Farnborough Town | The Dell, Southampton |
| 1980 | Newport | 2–2 aet[12] | Farnborough Town | The Dell, Southampton |
| Newport | 1-0 | Farnborough Town | Cams Alders, Fareham (Replay) |
| 1981 | Newport | 2–0 | Havant Town | The Dell, Southampton |
| 1982 | Farnborough Town | 2–0 | Basingstoke Town | The Dell, Southampton |
| 1983 | Sholing Sports | 3–1 | East Cowes Victoria Athletic | The Dell, Southampton |
| 1984 | Farnborough Town | 2–2 | Sholing Sports | The Dell, Southampton |
| Farnborough Town | 3–1 | Sholing Sports | Cams Alders, Fareham |
| 1985 | Waterlooville | 2–1 | Sholing Sports | The Dell, Southampton |
| 1986 | Farnborough Town | 2-0 | Basingstoke Town | The Dell, Southampton |
| 1987 | Portsmouth Reserves | 2–0 | Road-Sea Southampton | Fratton Park, Portsmouth |
| 1988 | Gosport Borough | 3–0 | Farnborough Town | The Dell, Southampton |
| 1989 | AFC Bournemouth Reserves | 2–1 | Basingstoke Town | Dean Court, Bournemouth |
| 1990 | Basingstoke Town | 8–0 | AFC Lymington | The Dell, Southampton |
| 1991 | Farnborough Town | 1–0 | Waterlooville | Fratton Park, Portsmouth |
| 1992 | Waterlooville | 1–0 | Havant Town | Fratton Park, Portsmouth |
| 1993 | Fareham Town | 4–1 | Farnborough Town | The Dell, Southampton |
| 1994 | Havant Town | 1–0 | Farnborough Town | The Dell, Southampton |
| 1995 | Havant Town | 1–0 | Farnborough Town | Fratton Park, Portsmouth |
| 1996 | Basingstoke Town | 2–0 | Waterlooville | The Dell, Southampton |
| 1997 | Basingstoke Town | 2–0 | Waterlooville | The Dell, Southampton |
| 1998 | Newport | 2–1 | Fareham Town | The Dell, Southampton |
| 1999 | Aldershot Town | 1–0 | Basingstoke Town | The Dell, Southampton |
| 2000 | Aldershot Town | 9–1 | Andover | The Camrose, Basingstoke |
| 2001 | Andover | 2–0 | Havant & Waterlooville | The Dell, Southampton |
| 2002 | Aldershot Town | 3–1 | Havant & Waterlooville | St Mary's Stadium, Southampton |
| 2003 | Aldershot Town | 2–1 | Bashley | St Mary's Stadium, Southampton |
| 2004 | Farnborough Town | 2–1 | Fareham Town | St Mary's Stadium, Southampton |
| 2005 | Winchester City | 2–1 | Aldershot Town | Dean Court, Bournemouth |
| 2006 | Farnborough Town | 1–0 | Basingstoke Town | Dean Court, Bournemouth |
| 2007 | Aldershot Town | 2–1 | Fleet Town | Dean Court, Bournemouth |
| 2008 | Basingstoke Town | 1–0 | Farnborough | Dean Court, Bournemouth |
| 2009 | Fleet Town | 1–0 | VT F.C. | St Mary's Stadium, Southampton |
| 2010 | AFC Totton | 4–0[13] | Aldershot Town | Dean Court, Bournemouth |
| 2011 | AFC Totton | 3–1[14] | Sholing | St Mary's Stadium, Southampton |
| 2012 | Eastleigh | 2–0[15] | AFC Totton | St Mary's Stadium, Southampton |
| 2013 | Alresford Town | 3–2[16] | AFC Bournemouth | Dean Court, Bournemouth |
| 2014 | Basingstoke Town | 3–2 aet[17] | Havant & Waterlooville | Fratton Park, Portsmouth |
| 2015 | Gosport Borough | 3–0 | Sholing | Fratton Park, Portsmouth |
| 2016 | Havant & Waterlooville | 1–1 (5–3 pens) | Winchester City | St Mary's Stadium, Southampton |
| 2017 | Basingstoke Town | 0–0 (7–6 pens)[18] | AFC Bournemouth | St Mary's Stadium, Southampton |
| 2018 | Havant & Waterlooville | 3–0[19] | Blackfield & Langley | St Mary's Stadium, Southampton |
| 2019 | Havant & Waterlooville | 2–1[20] | Basingstoke Town | Ten Acres, Eastleigh |
| 2020 | AFC Bournemouth | 2-2 (5–3 pens)[21][22] | Eastleigh | Snows Stadium, Totton |
| 2022 | Farnborough | 2–2 (4-1 pens) | Eastleigh | Ten Acres, Eastleigh |
| 2023 | Basingstoke Town | 1–0 | AFC Bournemouth | Fratton Park, Portsmouth |
| 2024 | AFC Portchester | 0–0 (5-4 pens) | AFC Totton | Recreation Ground (Aldershot) |
| 2025 | AFC Stoneham | 3-0 | AFC Portchester | Snows Stadium, Totton |