The J. Haig Gordon Cup is contested by member clubs of the Southern Counties FA. This year, only the thirteen South of Scotland League clubs have entered.
The format is straight knockout.
Edusport Academy’s South team (now known as Caledonian Braves) won the cup when it was last completed in 2018-19. The 2019-20 competition was abandoned and the cup was not contested in 2020-21.
- Lochmaben 0-2 Nithsdale Wanderers (Nov 27)
- Stranraer SOS 2-1 Mid Annandale (Nov 27)
- Upper Annandale 2-1 Newton Stewart (Nov 27)
- Wigtown & Bladnoch 1-4 Lochar Thistle (Nov 27)
- Abbey Vale 1-4 St Cuthbert Wanderers (Mar 12, aban Feb 5, post Nov 27)
- Creetown, Caledonian Braves SOS, Threave Rovers – byes
- Stranraer SOS 1-3 Nithsdale Wanderers (Feb 5)
- Upper Annandale 1-4 Lochar Thistle (Feb 5)
- Caledonian Braves SOS 1-0 Creetown (Feb 12)
- Threave Rovers 2-4 St Cuthbert Wanderers (Mar 23)
- Nithsdale Wanderers 4-1 Lochar Thistle (Apr 30)
- St Cuthbert Wanderers 4-2 Caledonian Braves (May 4)
- Nithsdale Wanderers 2-4 St Cuthbert Wanderers (May 13 @ Palmerston Park)