| 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 |
- |