| 1898-99 |
Cresswell Park |
6TH GALLOWAY RV |
6th Galloway RV - Douglas Wanderers 4-1 |
| 1899-00 |
Cresswell Park |
DUMFRIES HIBERNIAN |
Dumfries Hibernian - Douglas Wanderers 3-1 |
| 1900-01 |
Cresswell Park |
DOUGLAS WANDERERS |
Douglas Wanderers - Dumfries Hibernian 3-2 |
| 1901-02 |
Palmerstone Park |
VALE OF DRYFE |
Vale of Dryfe - Douglas Wanderers 2-1 |
| 1902-03 |
Dumfries |
VALE OF DRYFE |
Vale of Dryfe - &th Galloway RV 2-0 |
| 1903-04 |
- |
MAXWELLTOWN VOLUNTEERS |
Maxwelltown Volunteers - 6th Galloway RV |
| 1904-05 |
Dumfries |
DUMFRIES |
Dumfries - Thornhill 4-1 |
| 1905-06 |
Eastfield |
MAXWELLTOWN VOLUNTEERS |
Maxwelltown Volunteers - 6th Galloway RV 8-3 |
| 1906-07 |
- |
MAXWELLTOWN VOLUNTEERS |
- |
| 1907-08 |
- |
DUMFRIES |
Dumfries - Nithsdale Wanderers w/o |
| 1908-09 |
Dalbeattie |
DOUGLAS WANDERERS |
Douglas Wanderers - St Cuthbert Wanderers 5-3 |
| 1909-10 |
Palmerstone Park |
MID-ANNANDALE AMATEURS |
Mid-Annandale Amateurs - Dalbeattie Star 2-1 |
| 1910-11 |
Eastfield |
DOUGLAS WANDERERS |
Douglas Wanderers - 5th KOSB 4-4 (replay 4-1) |
| 1911-12 |
Dumfries |
DUMFRIES |
Dumfries - Thornhill 1-1 (replay 2-2) (replay 2-0) |
| 1912-13 |
Dumfries |
NITHSDALE WANDERERS |
Nithsdale Wanderers - Dalbeattie Star 0-0 (replay 5-0) |
| 1913-14 |
Dumfries |
SOLWAY STAR |
Solway Star - Thornhill 3-0 |
| 1914-15 |
Palmerstone Park |
MID-ANNANDALE |
batte Dumfries Amateurs 1-1 (replay 1-1 d.t.s.) (replay 6-2 d.t.s.) |
| 1915-16 |
non disputata |
| 1916-17 |
non disputata |
| 1917-18 |
non disputata |
| 1918-19 |
non disputata |
| 1919-20 |
Dumfries |
MID-ANNANDALE |
Mid-Annandale - Dalbeattie Star 3-1 |
| 1920-21 |
non completata |
| 1921-22 |
- |
QUEEN OF THE SOUTH |
Queen of the South - Douglas Wanderers 3-2 |
| 1922-23 |
- |
NEWTON STEWART |
Newton Stewart - Mid-Annandale |
| 1923-24 |
- |
NEWTON STEWART |
- |
| 1924-25 |
- |
NEWTON STEWART |
- |
| 1925-26 |
- |
ST CUTHBERT WANDERERS |
- |
| 1926-27 |
- |
ST CUTHBERT WANDERERS |
St Cuthbert Wanderers - Tarff Rovers |