| 1891-92 |
Recreation Ground |
5TH KIRKCUDBRIGHT RV |
5th KRV - Mid-Annandale 9-1 |
| 1892-93 |
Palmerston Park |
QUEEN OF THE SOUTH WANDERERS |
Queen of the South Wanderers - Newton Stewart Athletic 2-1 |
| 1893-94 |
Dumfries |
5TH KIRKCUDBRIGHT RV |
Queen of the South Wanderers - 5th KRV 2-2 (replay 1-4 |
| 1894-95 |
Palmerston Park |
MAXWELLTOWN THISTLE |
5th KRV - Maxwelltown Thistle 1-1 2-3 |
| 1895-96 |
Palmerston Park e Dalbeattie |
ST CUTHBERT WANDERERS |
St Cuthbert Wanderers - Douglas Wanderers 3-3 (replay 4-1) |
| 1896-97 |
Cresswell Park |
6TH GALLOWAY RV |
6th Galloway RV - St Cuthbert Wanderers 8-0 |
| 1897-98 |
Cresswell Park |
DUMFRIES |
Dumfries - Dumfries Hibernian 2-1 |
| 1898-99 |
Maxwelltown Park |
DUMFRIES |
Dumfries - Newton Stewart Athletic 4-1 |
| 1899-00 |
Dumfries |
DUMFRIES |
Dumfries - 6th Galloway RV 4-2 |
| 1900-01 |
Dumfries |
DUMFRIES |
Dumfries - 6th Galloway RV 4-3 |
| 1901-02 |
Cresswell Park |
DUMFRIES |
Dumfries - Maxwelltown Volunteers 3-0 |
| 1902-03 |
Dumfries |
DUMFRIES |
Dumfries - Douglas Wanderers 3-1 |
| 1903-04 |
Eastfield |
NITHSDALE WANDERERS |
Nithsdale Wanderers - Vale of Dryfe 4-1 |
| 1904-05 |
Dumfries |
MAXWELLTOWN VOLUNTEERS |
Maxwelltown Volunteers - 6th Galloway RV 2-1 |
| 1905-06 |
Dumfries |
DUMFRIES |
Dumfries - Nithsdale Wanderers 2-0 |
| 1906-07 |
Eastfield |
NITHSDALE WANDERERS |
Nithsdale Wanderers - Douglas Wanderers 1-0 |
| 1907-08 |
Dumfries |
MAXWELLTOWN VOLUNTEERS |
Maxwelltown Volunteers - Dalbeattie Star 5-1 |
| 1908-09 |
Dumfries |
DALBEATTIE STAR |
Dalbeattie Star - Nithsdale Wanderers 2-1 |
| 1909-10 |
Dumfries |
DUMFRIES |
Dumfries - Nithsdale Wanderers 1-0 |
| 1910-11 |
Palmerston Park |
NITHSDALE WANDERERS |
Nithsdale Wanderers - Dumfries 0-0 (replay 3-2) |
| 1911-12 |
Dumfries |
NITHSDALE WANDERERS |
Nithsdale Wanderers - Douglas Wanderers 1-1 (replay 1-0) |
| 1912-13 |
- |
SOLWAY STARS |
Solway Star - Dumfries 1-0 3-3 2-2 1-0 1-0 |
| 1913-14 |
Palmerston Park |
NITHSDALE WANDERERS |
Nithsdale Wanderers - Whithorn 4-3 |
| 1914-15 |
Dumfries |
5TH KOSB |
5th KOSB - Cuthbert Wanderers 1-1 (replay 2-1) |
| 1915-16 |
non disputata |
| 1916-17 |
non disputata |
| 1917-18 |
non disputata |
| 1918-19 |
non disputata |
| 2019-20 |
Dumfries |
NITHSDALE WANDERERS |
Nithsdale Wanderers - Cuthbert Wanderers 2-0 |
| 1920-21 |
- |
QUEEN OF THE SOUTH |
Queen of the South - Nithsdale Wanderers 1-0 |
| 1921-22 |
Dumfries e Sanquhar |
NITHSDALE WANDERERS |
Queen of the South - Nithsdale Wanderers 2-2 (replay 0-2) |
| 1922-23 |
- |
NITHSDALE WANDERERS |
- |
| 1923-24 |
- |
QUEEN OF THE SOUTH |
Queen of the South - Stranraer 5-2 |
| 1924-25 |
- |
DALBEATTIE STAR |
- |
| 1925-26 |
- |
STRANRAER |
Stranraer - St Cuthbert Wanderers 1-0 |
| 1926-27 |
- |
STRANRAER |
Stranraer - Thornhill 3-2 |
| 1927-28 |
Dumfries |
NITHSDALE WANDERERS |
Nithsdale Wanderer - Newton Stewart 8-0 |
| 1928-29 |
Dumfries |
MID-ANNANDALE |
Mid-Annandale - St Cuthbert Wanderers 2-0 |
| 1929-30 |
Dumfries |
ST CUTHBERT WANDERERS |
St Cuthbert Wanderers - Newton Stewart 4-1 |
| 1930-31 |
- |
DALBEATTIE STAR |
Dalbeattie Star - Stranraer 1-0 |
| 1931-32 |
- |
STRANRAER |
- |
| 1932-33 |
- |
STRANRAER |
- |
| 1933-34 |
- |
DALBEATTIE STAR |
- |
| 1934-35 |
- |
QUEEN OF THE SOUTH |
- |
| 1935-36 |
Dumfries |
QUEEN OF THE SOUTH |
Queen of the South - Creetown 4-2 |
| 1936-37 |
- |
STRANRAER |
Stranraer - St Cuthbert Wanderers 2-1 |
| 1937-38 |
- |
SOLWAY STAR |
- |
| 1938-39 |
Palmerston Park |
STRANRAER |
Stranraer - Solway Star 8-5 d.t.s. |
| 1939-40 |
non completata |
| 1940-41 |
non disputata |
| 1941-42 |
non disputata |
| 1942-43 |
non disputata |
| 1943-44 |
non disputata |
| 1944-45 |
non disputata |
| 1945-46 |
- |
NITHSDALE WANDERERS |
- |
| 1946-47 |
- |
DALBEATTIE STAR |
- |
| 1947-48 |
- |
STRANRAER |
- |
| 1948-49 |
- |
NEWTON STEWART |
Newton Stewart - Stranraer 1-0 |
| 1949-50 |
- |
TARFF ROVERS |
- |
| 1950-51 |
- |
NEWTON STEWART |
- |
| 1951-52 |
- |
TARFF ROVERS |
- |
| 1952-53 |
- |
ST CUTHBERT WANDERERS |
- |
| 1953-54 |
- |
ST CUTHBERT WANDERERS |
- |
| 1954-55 |
- |
WHITHORN |
- |
| 1955-56 |
- |
NEWTON STEWART |
- |
| 1956-57 |
- |
STRANRAER |
- |
| 1957-58 |
- |
GREYSTONE ROVERS |
- |
| 1958-59 |
- |
NEWTON STEWART |
- |
| 1959-60 |
- |
STRANRAER |
- |
| 1960-61 |
- |
STRANRAER |
- |
| 1961-62 |
- |
QUEEN OF THE SOUTH |
- |
| 1962-63 |
- |
NEWTON STEWART |
- |
| 1963-64 |
- |
STRANRAER |
- |
| 1964-65 |
- |
THREAVE ROVERS |
- |
| 1965-66 |
- |
QUEEN OF THE SOUTH |
- |
| 1966-67 |
- |
STRANRAER |
- |
| 1967-68 |
- |
TARFF ROVERS |
- |
| 1968-69 |
- |
STRANRAER |
- |
| 1969-70 |
- |
ST CUTHBERT WANDERERS |
- |
| 1970-71 |
- |
STRANRAER |
- |
| 1971-72 |
- |
QUEEN OF THE SOUTH |
- |
| 1972-73 |
- |
TARFF ROVERS |
- |
| 1973-74 |
- |
STRANRAER |
- |
| 1974-75 |
- |
TARFF ROVERS |
- |
| 1975-76 |
- |
QUEEN OF THE SOUTH |
- |
| 1976-77 |
- |
STRANRAER |
- |
| 1977-78 |
- |
LINCLUDEN SWIFT |
- |
| 1978-79 |
- |
LINCLUDEN SWIFT |
- |
| 1979-80 |
- |
THREAVE ROVERS |
- |
| 1980-81 |
- |
THREAVE ROVERS |
- |
| 1981-82 |
- |
QUEEN OF THE SOUTH |
- |
| 1982-83 |
- |
QUEEN OF THE SOUTH |
- |
| 1983-84 |
- |
NEWTON STEWART |
- |
| 1984-85 |
- |
CREETOWN |
- |
| 1985-86 |
- |
THREAVE ROVERS |
- |
| 1986-87 |
- |
QUEEN OF THE SOUTH |
- |
| 1987-88 |
- |
QUEEN OF THE SOUTH |
- |
| 1988-89 |
- |
STRANRAER |
- |
| 1989-90 |
- |
ANNAN ATHLETIC |
- |
| 1990-91 |
- |
QUEEN OF THE SOUTH |
- |
| 1991-92 |
- |
STRANRAER |
- |
| 1992-93 |
- |
DALBEATTIE STAR |
- |
| 1993-94 |
- |
STRANRAER |
- |
| 1994-95 |
- |
STRANRAER |
- |
| 1995-96 |
- |
ANNAN ATHLETIC |
- |
| 1996-97 |
- |
QUEEN OF THE SOUTH |
- |
| 1997-98 |
- |
THREAVE ROVERS |
- |
| 1998-99 |
- |
ANNAN ATHLETIC |
- |
| 1999-00 |
- |
QUEEN OF THE SOUTH |
- |
| 2000-01 |
non completata |
| 2001-02 |
- |
TARFF ROVERS |
- |
| 2002-03 |
- |
QUEEN OF THE SOUTH |
- |
| 2003-04 |
- |
QUEEN OF THE SOUTH |
- |
| 2004-05 |
- |
GRETNA |
- |
| 2005-06 |
- |
ANNAN ATHLETIC |
- |
| 2006-07 |
- |
DALBEATTIE STAR |
- |
| 2007-08 |
- |
THREAVE ROVERS |
- |
| 2008-09 |
- |
DALBEATTIE STAR |
- |
| 2009-10 |
- |
ST CUTHBERT WANDERERS |
- |
| 2010-11 |
- |
ANNAN ATHLETIC |
- |
| 2011-12 |
- |
DALBEATTIE STAR |
- |
| 2012-13 |
- |
DALBEATTIE STAR |
- |
| 2013-14 |
- |
WIGTOWN & BLADNOCH |
- |
| 2014-15 |
- |
QUEEN OF THE SOUTH |
- |
| 2015-16 |
- |
QUEEN OF THE SOUTH |
- |
| 2016-17 |
- |
DALBEATTIE STAR |
- |
| 2017-18 |
- |
DALBEATTIE STAR |
- |
| 2018-19 |
- |
BONNYTON THISTLE |
- |
| 2019-20 |
non completata |
| 2020-21 |
non disputata |
| 2021-22 |
- |
DALBEATTIE STAR |
- |
| 2022-23 |
- |
CALEDONIAN BRAVES |
Caledonian Braves - Dalbeattie Star 3-1 |
| 2023-24 |
- |
CALEDONIAN BRAVES |
Caledonian Braves - Newton Stewart 7-0 |