Gibraltar's main cup since the 1894/95 Merchants Cup; Rock Cup since 1935/36. Historical gaps remain unresolved.
| Season | Gibraltar Cup winner | Runner-up | Trophy |
|---|---|---|---|
| 2026/27 | - | - The Rock Cup is in progress; no winner has been decided. | — |
| 2025/26 | Lincoln Red Imps FC | Mons Calpe SC Final: 5-0. |  |
| 2024/25 | FCB Magpies | Lions Gibraltar FC Final: 3-1. | |
| 2023/24 | Lincoln Red Imps FC | Europa FC Final: 3-0. | — |
| 2022/23 | FCB Magpies | Lincoln Red Imps FC Final: 1-1. | — |
| 2021/22 | Lincoln Red Imps FC | FC Bruno's Magpies Final: 2-1. | — |
| 2020/21 | Lincoln Red Imps FC | Glacis United FC Final: 2-0. | — |
| 2019/20 | Abandoned The Rock Cup was abandoned; no winner was awarded. | ||
| 2018/19 | Europa FC | Gibraltar United Final: 3-0. | — |
| 2017/18 | Europa FC | Mons Calpe SC Final: 2-1. | — |
| 2016/17 | Europa FC | Lincoln Red Imps FC Final: 3-0. | — |
| 2015/16 | Lincoln Red Imps FC | Europa FC Final: 2-0. | — |
| 2014/15 | Lincoln Red Imps FC | Lynx FC Final: 4-1. | — |
| 2013/14 | Lincoln FC | College Europa FC Final: 1-0. |  |
| 2012/13 | St Joseph's FC | Manchester United FC Final: 3-1. | — |
| 2011/12 | St Joseph's FC | Lions Gibraltar FC Final: 2-0. | — |
| 2010/11 | Lincoln FC | Glacis United FC Final: 2-1. | — |
| 2009/10 | Lincoln FC | Gibraltar United Final: 5-1. | — |
| 2008/09 | Lincoln FC | Shamrock 101 FC Final: 4-0. | — |
| 2007/08 | Lincoln FC | PwC Laguna FC Final: 3-0. | — |
| 2006/07 | Newcastle FC | St Joseph's FC Final: 6-0. | — |
| 2005/06 | Newcastle FC | Glacis United FC Final: 1-1. | — |
| 2004/05 | Newcastle FC | Gibraltar United Final: 8-0. | — |
| 2003/04 | Newcastle FC | St Joseph's FC Final: 9-0. | — |
| 2002/03 | Manchester United FC | Newcastle FC Final: 2-2. | — |
| 2001/02 | Lincoln FC | Gibraltar United Final: 3-2. | — |
| 2000/01 | Gibraltar United | Lincoln FC Final: 0-0. | — |
| 1999/00 | Gibraltar United | Glacis United FC Final: 4-1. | — |
| 1998/99 | Gibraltar United | - Winner documented; the final score is not recorded. | — |
| 1997/98 | Glacis United FC | - Winner documented; the final score is not recorded. | — |
| 1996/97 | Glacis United FC | - Winner documented; the final score is not recorded. | — |
| 1995/96 | St Joseph's FC | - Winner documented; the final score is not recorded. | — |
| 1994/95 | St Theresa's FC | - Winner documented; the final score is not recorded. | — |
| 1993/94 | Lincoln FC | - Winner documented; the final score is not recorded. | — |
| 1992/93 | Lincoln FC | - Winner documented; the final score is not recorded. | — |
| 1991/92 | St Joseph's FC | - Winner documented; the final score is not recorded. | — |
| 1990/91 | - | - The winner is not recorded. | — |
| 1989/90 | Lincoln FC | - Winner documented; the final score is not recorded. | — |
| 1988/89 | Lincoln Reliance FC | - Winner documented; the final score is not recorded. | — |
| 1987/88 | RAF Gibraltar FC | - Winner documented; the final score is not recorded. | — |
| 1986/87 | St Joseph's FC | - Winner documented; the final score is not recorded. | — |
| 1985/86 | Lincoln FC | - Winner documented; the final score is not recorded. | — |
| 1984/85 | St Joseph's FC | - Winner documented; the final score is not recorded. | — |
| 1983/84 | St Joseph's FC | - Winner documented; the final score is not recorded. | — |
| 1982/83 | St Joseph's FC | - Winner documented; the final score is not recorded. | — |
| 1981/82 | Glacis United FC | - Winner documented; the final score is not recorded. | — |
| 1980/81 | Glacis United FC | - Winner documented; the final score is not recorded. | — |
| 1979/80 | Manchester United FC | - Winner documented; the final score is not recorded. | — |
| 1978/79 | St Joseph's FC | - Winner documented; the final score is not recorded. | — |
| 1977/78 | St Jago's United FC | - Winner documented; the final score is not recorded. | — |
| 1976/77 | Manchester United FC | - Winner documented; the final score is not recorded. | — |
| 1975/76 | 2nd Battalion Royal Green Jackets FC | - Winner documented; the final score is not recorded. | — |
| 1974/75 | Glacis United FC | - Winner documented; the final score is not recorded. | — |
| 1973/74 | Manchester United Reserves FC | - Winner documented; the final score is not recorded. | — |
| 1972/73 | - | - Rock Cup not held. | — |
| 1971/72 | - | - Rock Cup not held. | — |
| 1970/71 | - | - Rock Cup not held. | — |
| 1969/70 | - | - Rock Cup not held. | — |
| 1968/69 | - | - Rock Cup not held. | — |
| 1967/68 | - | - Rock Cup not held. | — |
| 1966/67 | - | - Rock Cup not held. | — |
| 1965/66 | Gibraltar United | - Winner documented; the final score is not recorded. | — |
| 1964/65 | Gibraltar United | - Winner documented; the final score is not recorded. | — |
| 1963/64 | Gibraltar United | - Winner documented; the final score is not recorded. | — |
| 1962/63 | Gibraltar United | - Winner documented; the final score is not recorded. | — |
| 1961/62 | FC Britannia XI | - Winner documented; the final score is not recorded. | — |
| 1960/61 | Europa FC | - Winner documented; the final score is not recorded. | — |
| 1959/60 | Prince of Wales FC | - Winner documented; the final score is not recorded. | — |
| 1958/59 | Gibraltar United | Europa FC Final: 5-3. | — |
| 1957/58 | Europa FC | - Winner documented; the final score is not recorded. | — |
| 1956/57 | - | - Rock Cup apparently not held. | — |
| 1955/56 | St Joseph's FC | - Winner documented; the final score is not recorded. | — |
| 1954/55 | FC Britannia XI | - Winner documented; the final score is not recorded. | — |
| 1953/54 | Gibraltar United | - Winner documented; the final score is not recorded. | — |
| 1952/53 | - | - Rock Cup apparently not held. | — |
| 1951/52 | Europa FC | Gibraltar United Final: 1-0. | — |
| 1950/51 | Europa FC | Prince of Wales FC Final: 2-1. | — |
| 1949/50 | Europa FC | Prince of Wales FC Final: 2-0. | — |
| 1948/49 | Prince of Wales FC | FC Britannia XI Final: 4-2. | — |
| 1947/48 | FC Britannia XI | Europa FC Final: 2-1. | — |
| 1946/47 | Gibraltar United | - Winner documented; the final score is not recorded. | — |
| 1945/46 | Europa FC | - Winner documented; the final score is not recorded. | — |
| 1944/45 | - | - Rock Cup not held. | — |
| 1943/44 | 4th Battalion Royal Scots FC | - Winner documented; the final score is not recorded. | — |
| 1942/43 | RAF New Camp | - Winner documented; the final score is not recorded. | — |
| 1941/42 | AARA FC | - Winner documented; the final score is not recorded. | — |
| 1940/41 | - | - Rock Cup not held. | — |
| 1939/40 | FC Britannia XI | - Winner documented; the final score is not recorded. | — |
| 1938/39 | 2nd Battalion King's Regiment FC | - Winner documented; the final score is not recorded. | — |
| 1937/38 | Europa FC | HMS Hood FC Winner documented; the final score is not recorded. | — |
| 1936/37 | FC Britannia XI | - Winner documented; the final score is not recorded. | — |
| 1935/36 | HMS Hood FC | - Winner documented; the final score is not recorded. The opponent was a Gibraltar FA representative XI, not an independent club. | — |
| 1933/34 | Electricity Department FC | - Winner documented; the final score is not recorded. | — |
| 1926/27 | Europa FC | - Winner documented; the final score is not recorded. | — |
| 1907/08 | FC Britannia XI | - Winner documented; the final score is not recorded. | — |
| 1905/06 | Prince of Wales FC | - Winner documented; the final score is not recorded. | — |
| 1904/05 | Athletic FC | - Winner documented; the final score is not recorded. | — |
| 1903/04 | Prince of Wales FC | - Winner documented; the final score is not recorded. | — |
| 1902/03 | Prince of Wales FC | - Winner documented; the final score is not recorded. | — |
| 1901/02 | Exiles FC | - Winner documented; the final score is not recorded. | — |
| 1900/01 | Prince of Wales FC | - Winner documented; the final score is not recorded. | — |
| 1899/00 | Exiles FC | - Winner documented; the final score is not recorded. | — |
| 1898/99 | Albion FC | - Winner documented; the final score is not recorded. | — |
| 1897/98 | Jubilee FC | - Winner documented; the final score is not recorded. | — |
| 1896/97 | Jubilee FC | - Winner documented; the final score is not recorded. | — |
| 1894/95 | Gibraltar FC | Jubilee FC Winner documented; the final score is not recorded. | — |
