| 1903 | KIRKWALL | STROMNESS | CH AKROYD | JS CLOUSTON | RH PRYDE | J FIDDLER | 2 CLUBS PLAYED FOR CUP KIRKWALL & STROMNESS |
| 1904 | STROMNESS | STROMNESS | CH AKROYD | JS CLOUSTON | GG BAILLLIE | J FIDDLER | - |
| - | - | JW STOVE | J MATCHES | D MACPHERSON | JDC FALCONER | - |
| 1905 | STROMNESS | STROMNESS | CH AKROYD | JS CLOUSTON | FC CRAWFORD | RH PRYDE | - |
| 1906 | STROMNESS | STROMNESS | CH AKROYD | JS CLOUSTON | FC CRAWFORD | J HEPBURN | - |
| - | - | GG BAILLIE | JA MOWAT | J FIDDLER | JDC FALCONER | - |
| 1907 | STROMNESS | STROMNESS | CH AKROYD | W KIDD | FC CRAWFORD | J LEASK | - |
| - | - | J FIDDLER | D HEPBURN | GG BAILLLIE | W SHEPHERD | - |
| 1908 | STROMNESS | STROMNESS | JW LEASK | J HEPBURN | D HEPBURN | J FIDDLER | WICK ENTERED COMPETITION |
| 1909 | STROMNESS | STROMNESS | J FIDDLER | JW SHEPHERD | JW LEASK | J HEPBURN | - |
| 1910 | STROMNESS | STROMNESS | JW LEASK | I SCOTT | J FIDDLER | F WATSON | THURSO ENTERED COMPETITION |
| 1911 | STROMNESS | KIRKWALL | J FLETT | J WHITE | F BUCHANAN | J INKSTER | - |
| 1912 | - | WICK | D MACKAY | D DURRAN | A JOHNSTONE | WG REID | - |
| 1913 | - | WICK | A JOHNSTONE | WG REID | D CAMERON | J COWANS | - |
| 1919 | - | KIRKWALL | J WHITE | J INKSTER | CMDR RF WHITE RN | LIEUT JD CAMPBELL RN | - |
| 1920 | - | WICK | WG REID | DR J C McGREGOR | T CLEESON | J WATERS | - |
| 1921 | - | WICK | WG REID | DR J C McGREGOR | T CLEESON | J WATERS | - |
| 1922 | - | STROMNESS | J MATCHES | W SINCLAIR | TR MOWAT | AC HEPBURN | - |
| 1923 | - | KIRKWALL | J GOW | Wm SUTHERLAND | NA PARKER | JS RUTHERFORD | - |
| 1924 | - | THURSO | Dr MACDONALD | A JOHNSTON | R BRODIE | W REID | - |
| 1925 | - | KIRKWALL | JD BRASS | J INKSTER | J WHITE | A CLARK | - |
| 1926 | - | WICK | W SEMPLE | D ROSS | Dr MACGREGOR | A MATHESON | - |
| 1927 | - | STROMNESS | W SINCLAIR | J GRAY | A SMITH | JM DREVER | - |
| 1928 | - | WICK | WW SEMPLE | A MATHESON | J WATERS | AM FIDDLER | - |
| 1929 | - | KIRKWALL | JD BRASS | A CLARK | IC McCLURE | GE CUMMING | - |
| 1930 | - | THURSO | W REID | DB KEITH | A GUNN | AM MACKAY | - |
| 1931 | - | KIRKWALL | JD BRASS | JW TULLOCH | A CLARK | WH TULLOCH | - |
| 1932 | - | KIRKWALL | JD BRASS | A CLARK | WH TULLOCH | W COLLIER | - |
| 1933 | THURSO | WICK | WW SEMPLE | A SUTHERLAND | A MATHESON | D SKINNER | - |
| 1934 | STROMNESS | WICK | A SUTHERLAND | R FINLAYSON | J LAMONT | A MATHESON | CUP WENT MISSING - COMPETITION SUSPENDED |
| 1935 | - | - | - | - | - | - | - |
| 1936 | - | - | - | - | - | - | - |
| 1937 | - | - | - | - | - | - | - |
| 1938 | - | - | - | - | - | - | CUP FOUND |
| 1939 | - | - | - | - | - | - | SECOND WORLD WAR - NOT PLAYED |
| 1940 | - | - | - | - | - | - | SECOND WORLD WAR - NOT PLAYED |
| 1941 | - | - | - | - | - | - | SECOND WORLD WAR - NOT PLAYED |
| 1942 | - | - | - | - | - | - | SECOND WORLD WAR - NOT PLAYED |
| 1943 | - | - | - | - | - | - | SECOND WORLD WAR - NOT PLAYED |
| 1944 | - | - | - | - | - | - | SECOND WORLD WAR - NOT PLAYED |
| 1945 | - | - | - | - | - | - | SECOND WORLD WAR - NOT PLAYED |
| 1946 | - | - | - | - | - | - | NOT PLAYED |
| 1947 | - | - | - | - | - | - | NOT PLAYED |
| 1948 | - | - | - | - | - | - | NOT PLAYED |
| 1949 | - | - | - | - | - | - | NOT PLAYED |
| 1950 | - | - | - | - | - | - | NOT PLAYED |
| 1951 | - | - | - | - | - | - | NOT PLAYED |
| 1952 | - | - | - | - | - | - | NOT PLAYED |
| 1953 | - | WICK | WG GRANT | CN MINTO | D SINCLAIR | WJ MILLER | - |
| 1954 | - | KIRKWALL | Dr DM SIBBALD | JW MACKAY | G DONALDSON | A TINCH | - |
| 1955 | - | THURSO | R STEWART | W STEWART | R BELL | WA McGREGOR | - |
| 1956 | - | - | - | - | - | - | NO RECORDS |
| 1957 | - | KIRKWALL | WAD TINCH | JW MACKAY | JP FLETT | G DONALDSON | - |
| 1958 | - | WICK | CN MINTO | D SINCLAIR | CA ROSS | WJ MILLER | - |
| 1959 | - | KIRKWALL | IH McCLURE | JA CHEYNE | JJ SINCLAIR | G DONALDSON JR | - |
| 1960 | - | THURSO | G JARDINE | W STEWART | R ALLARDYCE | R BELL | REAY ENTERED COMPETITION SOMETIME IN 1960s |
| 1961 | - | THURSO | RH ALLARDYCE | R BELL | G JARDINE | J DOUGAL | - |
| 1962 | - | KIRKWALL | G DONALDSON JR | JW MACKAY | D SINCLAIR | DR JH GRANT | - |
| 1963 | - | KIRKWALL | G DONALDSON JR | JW MACKAY | D SINCLAIR | DR JH GRANT | - |
| 1964 | - | KIRKWALL | G DONALDSON JR | JW MACKAY | JP FLETT | DR JH GRANT | - |
| 1965 | - | STROMNESS | R MOWAT | O TAIT | J WRIGHT | R SMITH | - |
| 1966 | - | REAY | JB NIVEN | J ANDERSON | J O'NEILL | J ROBERTSON | - |
| 1967 | KIRKWALL | STROMNESS | OS TAIT | SM YOUNG | RS MOWAT | J SUTHERLAND | - |
| 1968 | WICK | THURSO | D SPIERS | R ALLARDICE | W STEWART | D THOM | - |
| 1969 | STROMNESS | STROMNESS | OS TAIT | RS MOWAT | R WILSON | J SUTHERLAND | - |
| 1970 | THURSO | THURSO | DG SPIERS | G ROSS | N KIRKPATRICK | WS STEWART | - |
| 1971 | KIRKWALL | REAY | WJ DONALD | D MCLEOD | A POLLOCK | G McKILLIGIN | - |
| 1972 | REAY | KIRKWALL | G CAIRNS | DA ROSS | W LIDDLE | A STOCKAN | - |
| 1973 | STROMNESS | STROMNESS | R WILSON | OS TAIT | RS MOWAT | J SUTHERLAND | - |
| 1974 | WICK | WICK | J BEALES | G DICKSON | W GUNN | JA MILLER | - |
| 1975 | KIRKWALL | STROMNESS | R WILSON | J SUTHERLAND | OS TAIT | RS MOWAT | - |
| 1976 | THURSO | WICK | J BEALES | G McKIDDIE | DD SHEARER | R SUTHERLAND | - |
| 1977 | STROMNESS | WICK | WS MOWAT | G McKIDDIE | J SUTHERLAND | R SUTHERLAND | - |
| 1978 | REAY | THURSO | E NEWMAN | GA DUNNETT | A DUNNETT | D CALDER | - |
| 1979 | KIRKWALL | KIRKWALL | R BULLEN | SM FOTHERINGHAME | KD PEACE | JS KEMP | SHETLAND ENTERED COMPETITION |
| 1980 | WICK | WICK | R TAYLOR | R BARKER | G McKIDDIE | J BEALES | - |
| 1981 | STROMNESS | KIRKWALL | R BULLEN | EI DONALDSON | SM FOTHERINGHAME | KD PEACE | - |
| 1982 | THURSO | THURSO | GA DUNNETT | E NEWMAN | N McNAIR | A URQUHART | - |
| 1983 | REAY | THURSO | GA DUNNETT | E NEWMAN | A URQUHART | S SPARGO | - |
| 1984 | SHETLAND | THURSO | GA DUNNETT | E NEWMAN | A URQUHART | S SPARGO | - |
| 1985 | KIRKWALL | WICK | B GARDNER | C PRITCHARD | M MacDONALD | R TAYLOR | - |
| 1986 | WICK | STROMNESS | ME CROY | FGS FLETT | EW SUTHERLAND | SJC TAYLOR | - |
| 1987 | STROMNESS | KIRKWALL | KD PEACE | EI DONALDSON | G RENDALL | SM FOTHERINGHAME | - |
| 1988 | THURSO | THURSO | GA DUNNETT | A URQUHART | A LOGIE | S SPARGO | - |
| 1989 | SHETLAND | SHETLAND | JS SINCLAIR | G SANDISON | J JOHNSTON | P SINCLAIR | - |
| 1990 | REAY | KIRKWALL | DA ROBERTSON | P McKINLAY | J RUSSELL | SM FOTHERINGHAME | - |
| 1991 | KIRKWALL | KIRKWALL | SM FOTHERINGHAME | G RENDALL | J RUSSELL | EI DONALDSON | - |
| 1992 | WICK | REAY | DA MACKAY | NH McDONALD | G MAXWELL | D SPIERS | - |
| 1993 | STROMNESS | REAY | R TAYLOR | C PATERSON | DA MACKAY | J HENDERSON | - |
| 1994 | THURSO | WICK | RW TAYLOR | LW MAIN | E LARNACH | R BEAMES | - |
| 1995 | SHETLAND | SHETLAND | IG SANDISON | M BOXWELL | M MACKENZIE | D HUTCHEON | - |
| 1996 | REAY | REAY | DM BEATON | J HENDERSON | C PATERSON | RS TAYLOR | - |
| 1997 | KIRKWALL | WICK | RW TAYLOR | N KLIMAS | J HUNTER | DA MACKAY | - |
| 1998 | WICK | WICK | J HUNTER | RW TAYLOR | N KLIMAS | R BEAMES | - |
| 1999 | STROMNESS | REAY | GA DUNNETT | J HENDERSON | DA MACKAY | C PATERSON | - |
| 2000 | THURSO | WICK | RW TAYLOR | L MAIN | J HUNTER | S BARKER | - |
| 2001 | SHETLAND | WICK | LT MAIN | S BARKER | RW TAYLOR | N KLIMAS | - |
| 2002 | REAY | WICK | RW TAYLOR | N KLIMAS | L MAIN | S BARKER | - |
| 2003 | KIRKWALL | REAY | GA DUNNETT | J HENDERSON | DA MACKAY | RS TAYLOR | - |
| 2004 | WICK | WICK | JA HARPER | N KLIMAS | RW TAYLOR | W MURRAY | - |
| 2005 | STROMNESS | WICK | W MURRAY | RW TAYLOR | N KLIMAS | JA HARPER | LYBSTER & WHALSAY ENTERED COMPETITION |
| 2006 | THURSO | KIRKWALL | S RENDALL | KJ SINCLAIR | M FLEET | P McKINLAY | - |
| 2007 | SHETLAND | THURSO | BH MUNRO | DJ THORBURN | AM SWANSON | JD SANGSTER | - |
| 2008 | REAY | THURSO | BH MUNRO | DJ THORBURN | AM SWANSON | JD SANGSTER | - |
| 2009 | KIRKWALL | KIRKWALL | S SLATER | M McGINN | S RENDALL | G FLETT | - |
| 2010 | WICK | THURSO | AM SWANSON | JD SANGSTER | PSD SANGSTER | DJ THORBURN | - |
| 2011 | WHALSAY | THURSO | AM SWANSON | JD SANGSTER | DG DUNBAR | PSD SANGSTER | - |
| 2012 | LYBSTER | THURSO | AM SWANSON | JD SANGSTER | DG DUNBAR | PSD SANGSTER | - |
| 2013 | STROMNESS | KIRKWALL | S SLATER | P McKINLAY | S RENDALL | EC RENDALL | - |
| 2014 | THURSO | THURSO | DJ THORBURN | AM SWANSON | JD SANGSTER | DG DUNBAR | - |
| 2015 | SHETLAND | REAY | GA DUNNETT | T ROSS | G SUTHERLAND | RS TAYLOR | - |
| 2016 | REAY | THURSO | DJ THORBURN | DG DUNBAR | AM SWANSON | JD SANGSTER | - |
| 2017 | KIRKWALL | KIRKWALL | S RENDALL | P McKINLAY | E RENDALL | A BONNER | |
| 2018 | WICK | KIRKWALL | S RENDALL | A BONNER | S SLATER | E RENDALL | |
| 2019 | WHALSAY | WICK | D THORBURN | G STEVEN | N KLIMAS | A LARNACH | |
| 2020 | LYBSTER | NOT PLAYED | | | | | |
| 2021 | | | | | | | |
| 2022 | | | | | | | |
| 2023 | | | | | | | |
| 2024 | DALE | KIRKWALL | M Schinkel | S Rendall | L Findlay | S Walls | |
