{| class="wikitable sortable" style="text-align:center;"
|-
!Sæson
!Vinder
|-
|1934–35
|[[Chief Construction F.C.]] (1)
|-
|1935–36
|[[Chief Constructor F.C.]] (1)
|-
|1936–37
|[[FC Britannia XI]] (6)
|-
|1937–38
|[[Europa F.C.]] (5)
|-
|1938–39
|[[Prince of Wales F.C.]] (17)
|-
|1939–40
|[[Prince of Wales F.C.]] (18)
|-
|1940–41
|[[FC Britannia XI]] (7)
|-
|1941–46
|''No competition''
|-
|1946–47
|[[Gibraltar United F.C.]] (1)
|-
|1947–48
|[[Gibraltar United F.C.]] (2)
|-
|1948–49
|[[Gibraltar United F.C.]] (3)
|-
|1949–50
|[[Gibraltar United F.C.]] (4)
|-
|1950–51
|[[Gibraltar United F.C.]] (5)
|-
|1951–52
|[[Europa F.C.]] (6)
|-
|1952–53
|[[Prince of Wales F.C.]] (19)
|-
|1953–54
|[[Gibraltar United F.C.]] (6)
|-
|1954–55
|[[FC Britannia XI]] (8)
|-
|1955–56
|[[FC Britannia XI]] (9)
|-
|1956–57
|[[FC Britannia XI]] (10)
|-
|1957–58
|[[FC Britannia XI]] (11)
|-
|1958–59
|[[FC Britannia XI]] (12)
|-
|1959–60
|[[Gibraltar United F.C.]] (7)
|-
|1960–61
|[[FC Britannia XI]] (13)
|-
|1961–62
|[[Gibraltar United F.C.]] (8)
|-
|1962–63
|[[FC Britannia XI]] (14)
|-
|1963–64
|[[Gibraltar United F.C.]] (9)
|-
|1964–65
|[[Gibraltar United F.C.]] (10)
|-
|1965–66
|[[Glacis United F.C.]] (1)
|-
|1966–67
|[[Glacis United F.C.]] (2)
|-
|1967–68
|[[Glacis United F.C.]] (3)
|-
|1968–69
|[[Glacis United F.C.]] (4)
|-
|1969–70
|[[Glacis United F.C.]] (5)
|-
|1970–71
|[[Glacis United F.C.]] (6)
|-
|1971–72
|[[Glacis United F.C.]] (7)
|-
|1972–73
|[[Glacis United F.C.]] (8)
|-
|1973–74
|[[Glacis United F.C.]] (9)
|-
|1974–75
|[[Manchester 62 F.C.]] (1)
|-
|1975–76
|[[Glacis United F.C.]] (10)
|-
|1976–77
|[[Manchester 62 F.C.]] (2)
|}
Historie Foreninger Organisationer