The Tweedie Cup is contested by the member clubs of the South of Scotland League, currently on a bi-annual basis.
Bonnyton Thistle and Edusport Academy SOS have not entered, giving an entry of fourteen clubs this season.
The format is straight knockout. Stranraer won the competition when it was last contested in 2017-18.
First Round (Aug 28 unless stated)
- Stranraer SOS 2-1 Abbey Vale (@ Stranraer Acad) (Aug 27)
- Dumfries YMCA 0-2 Heston Rovers
- Lochar Thistle 0-3 Upper Annandale
- Newton Stewart 2-1 Mid Annandale
- Threave Rovers 2-3 Nithsdale Wanderers
- Wigtown & Bladnoch 0-5 St Cuthbert Wanderers (Aug 31)
Second Round (Oct 26)
- Newton Stewart 0-3 Lochmaben
- Nithsdale Wanderers 3-2 St Cuthbert Wanderers
- Upper Annandale 4-0 Creetown
- Heston Rovers 2-1 Stranraer SOS (Oct 27)
- Heston Rovers – Upper Annandale
- Nithsdale Wanderers – Lochmaben