The Southern Counties Challenge Cup is contested by the member clubs of the South of Scotland League and other senior clubs who are members of the Southern Counties FA.
The format is straight knockout.
Bonnyton Thistle are the current Cup holders following their 2018-19 win, though they now play in the West of Scotland League and no longer enter. The 2019-20 competition was abandoned and there was no competition in 2020-21.
First Round (Jan 22)
- Queen of the South 6-1 St Cuthbert Wanderers (Jan 18)
- Abbey Vale 1-4 Caledonian Braves
Mid Annandale – Stranraer SOS
Newton Stewart 1-1(6-7p) Creetown
- Nithsdale Wanderers 3-0 Lochar Thistle
Threave Rovers 2-3 Upper Annandale
- Dalbeattie Star 4-0 Lochmaben (Feb 9 @ Palmerston Park, post Jan 22)
Wigtown & Bladnoch – bye
- Queen of the South 0-1 Caledonian Braves (Mar 29)
- Wigtown & Bladnoch 0-8 Upper Annandale (Apr 6)
- Dalbeattie Star 6-1 Stranraer SOS (Apr 20)
- Nithsdale Wanderers 1-0 Creetown (Apr 23)
- Nithsdale Wanderers 2-3 Dalbeattie Star (May 4)
- Upper Annandale 0-3 Caledonian Braves (May 4)
- Caledonian Braves 2-3 Dalbeattie Star (May 14 @ Galabank, Annan)