| 1898-99 |
- |
6TH GALLOWAY RIFLE VOLUNTEERS |
6th Galloway Rifle Volunteers - Newton Stewart Athletic 5-5 (replay) |
| 1899-00 |
Dalbeattie |
DUMFRIES |
Dumfries - Dumfries Hibernian 5-3 |
| 1900-01 |
- |
DUMFRIES |
Dumfries - Dumfries Hibernian 4-2 |
| 1901-02 |
Dalbeattie |
DOUGLAS WANDERERS |
Dougla Wanderers - Dumfries 0-0 (replay 3-1) |
| 1902-03 |
- |
MAXWELLTOWN VOLUNTEERS |
Nithsdale Wanderers - Maxwelltown Volunteers 1-4 |
| 1903-04 |
Dumfries |
MAXWELLTOWN VOLUNTEERS |
Dumfries - Maxwelltown Volunteers 1-2 |
| 1904-05 |
Dalbeattie |
DUMFRIES |
Dumfries - Douglas Wanderers 0-0 (replay 2-1) |
| 1905-06 |
Dalbeattie |
DUMFRIES |
Dumfries - Nithsdale Wanderers 6-0 |
| 1906-07 |
- |
NEWTON STEWART |
Newton Stewart - Douglas Wanderers w/o |
| 1907-08 |
- |
MAXWELLTON VOLUNTEERS |
Maxwelltown Volunteers - Dumfries w/o |
| 1908-09 |
- |
ST CUTHBERT WANDERERS |
St Cuthbert Wanderers - Dumfries w/o |
| 1909-10 |
non disputata |
| 1910-11 |
sostituita dalla Southern Counties League |
| 1911-12 |
Dalbeattie |
DALBEATTIE |
Dalbeattie - Mid-Annandale 3-3 (replay 3-2) |
| 1912-13 |
non disputata |
| 1913-14 |
non disputata |
| 1914-15 |
non disputata |
| 1915-16 |
non disputata |
| 1916-17 |
non disputata |
| 1917-18 |
non disputata |
| 1918-19 |
non disputata |
| 1919-20 |
non disputata |
| 1920-21 |
non disputata |
| 1921-22 |
non disputata |
| 1922-23 |
non disputata |
| 1923-24 |
- |
STRANRAER |
Stranraer - St Cuthbert Wanderers |
| 1924-25 |
- |
ST CUTHBERT WANDERERS |
- |
| 1925-26 |
Stranraer |
ST CUTHBERT WANDERERS |
St Cuthbert Wanderers - Stranraer 4-0 |
| 1926-27 |
- |
ST CUTHBERT WANDERERS |
St Cuthbert Wanderers - Stranraer |
| 1927-28 |
- |
DALBEATTIE STAR |
Dalbeattie Star - St Cuthbert Wanderers 1-1 (replay 2-1) |
| 1928-29 |
- |
DALBEATTIE STAR |
- |
| 1929-30 |
- |
ST CUTHBERT WANDERERS |
- |
| 1930-31 |
- |
DALBEATTIE STAR |
Dalbeattie Star - Solway Star 1-1 (replay 3-2) |