La Wigtownshire Cup era una competizione calcistica organizzata dalla Wigtownshire Football Association. Originariamente riservata ai clubs della contea del Wigtownshire, successivamente accolse anche clubs del Kirkcudbrightshire.

 

1889-90 Whithorn NEWTON-STEWART ATHLETIC Newton-Stewart Athletic - Whithorn 2-1
1890-91 Holm Park - Newton-Stewart TARFF ROVERS Tarff Rovers - Garliestown 6-2
1891-92 Westwood Park - Stranraer NEWTON-STEWART ATHLETIC Newton-Stewart Athletic - Stranraer 4-0
1892-93 - GARLIESTOWN Garliestown - Newton-Stewart Athletic
1893-94 Holm Park - Newton-Stewart GARLIESTOWN Newton-Stewart Athletic - Garliestown 0-1
1894-95 Ballgreen Park - Stranraer GARLIESTOWN Garliestown - Tarff Rovers 8-5
1895-96 Whithorn NEWTON-STEWART ATHLETIC Newton-Stewart Athletic - Tarff Rovers 4-0
1896-97 - NEWTON-STEWART ATHLETIC Newton-Stewart Athletic - Glenarnott Thistle
1897-98 Stranraer NEWTON-STEWART ATHLETIC Stranraer - Newton-Stewart Athletic 1-2
1898-99 - STRANRAER -
1899-00 Holm Park - Newton-Stewart NEWTON-STEWART ATHLETIC Newton-Stewart Athletic - Stranraer 6-2
1900-01 Recreation Ground - Stranraer STRANRAER Stranraer - Tarff Rovers 3-2 d.t.s. (2-2)
1901-02 Whithorn TARFF ROVERS Tarff Rovers - Stranraer 3-1
1902-03 Holm Park - Newton-Stewart NEWTON-STEWART Wigtown - Newton-Stewart 0-5
1903-04 Holm Park - Newton-Stewart NEWTON-STEWART Newton-Stewart - Wigtown 8-1
1904-05 Holm Park - Newton-Stewart STRANRAER Stranraer - Tarff Rovers 2-2 (replay 3-2)
1905-06 Newton-Stewart STRANRAER Stranraer - Newton-Stewart 5-3 d.t.s. (3-3)
1906-07 Garliestown e Kirkcowan WHITHORN Whithorn - Newton-Stewart 1-1 (replay 1-1 1-0)
1907-08 Holm Park - Newton-Stewart WHITHORN Whithorn - Garlieston 2-1
1908-09 Stranraer NEWTON-STEWART Tarff Rovers - Newton-Stewart 5-2 (contestata) (replay 1-2)
1909-10 Kirkcowan STRANRAER Stranraer - Wigtown United 9-1
1910-11 Holm Park - Newton-Stewart STRANRAER Stranraer - Whithorn 4-1
1911-12 Wigtown NEWTON-STEWART Newton-Stewart - Whithorn 3-1
1912-13 - WHITHORN -
1913-14 Wigtown NEWTON-STEWART Newton-Stewart - Garlieston Excelsior 0-0 (replay 1-0)
1914-15 non disputata
1915-16 non disputata
1916-17 non disputata
1917-18 non disputata
1918-19 non disputata
1919-20  Stranraer STRANRAER  Stranraer - Whithorn 2-0 
1920-21 - STRANRAER Stranraer - Whithorn 2-0
1921-22 Kirkcowan NEWTON-STEWART Newton-Stewart - Stranraer 3-2
1922-23 Holm Park - Newton-Stewart TARFF ROVERS  Tarff Rovers - Wigtown & Bladnoch 0-0 (replay -) 
1923-24 Holm Park - Newton-Stewart STRANRAER Stranraer - Creetown 3-1
1924-25 - WIGTOWN & BLADNOCH Wigtown & Bladnoch - Newton-Stewart
1925-26 - NEWTON-STEWART Newton-Stewart - Stranraer 3-2
1926-27 - STRANRAER Creetown - Stranraer 2-2 (replay 2-2 1-4)
1927-28 Holm Park - Newton-Stewart STRANRAER Stranraer - Creetown 5-2
1928-29 non disputata
1929-30 Wigtown NEWTON-STEWART  Newton-Stewart - Garlieston 3-2 
1930-31 - WIGTOWN & BLADNOCH -
1931-32 non disputata
1932-33 - WIGTOWN & BLADNOCH Wigtown & Bladnoch - Stranraer
1933-34 - WIGTOWN & BLADNOCH Wigtown & Bladnoch - Newton-Stewart 4-0
1934-35 - CREETOWN -
1935-36 - CREETOWN -
1936-37 - ST CUTHBERT WANDERERS -
1937-38 - ST CUTHBERT WANDERERS -
1938-39 Cassencarrie Park - Creetown RAF WEST FREUGH RAF West Freugh - St Cuthbert Wanderers 7-2
1939-40 non disputata
1940-41 non disputata
1941-42 non disputata
1942-43 non disputata
1943-44 non disputata
1944-45 non disputata
1945-46  -  ST CUTHBERT WANDERERS  Newton-Stewart - St Cuthberth Wanderers 4-2 1-3 (spareggio 1-3) 
1946-47 non disputata
1947-48 -  STRANRAER  - 
1948-49 - WIGTOWN & BLADNOCH -
1949-50 non disputata
1950-51  -  NEWTON-STEWART  - 
1951-52 non disputata
1952-53 non disputata
1953-54 non disputata
1954-55  -  WHITHORN  - 
1955-56 non disputata
1956-57 non disputata
1957-58 non disputata
1958-59 non disputata
1959-60  -  THREAVE ROVERS  - 
1960-61 - STRANRAER RES -
1961-62 non disputata
1962-63 - TARFF ROVERS -
1963-64 non disputata
1964-65 - THREAVE ROVERS -
1965-66 non disputata
1966-67 non disputata
1967-68 - NEWTON STEWART -