| 1 | Sat 8 Sep 2018 | 0-3 v ArbroathArbroath 3-0 Annan Athletic | IRN-BRU Cup Second Round |
| 2 | Sat 24 Nov 2018 | 0-0 v MontroseMontrose 0-0 Annan Athletic | William Hill Scottish Cup Third Round |
| 3 | Sat 22 Dec 2018 | 4-0 v Berwick RangersAnnan Athletic 4-0 Berwick Rangers | Ladbrokes League Two |
| 4 | Sat 5 Jan 2019 | 2-0 v Elgin CityAnnan Athletic 2-0 Elgin City | Ladbrokes League Two |
| 5 | Sat 26 Jan 2019 | 5-0 v Albion RoversAlbion Rovers 0-5 Stirling Albion | Ladbrokes League Two |
| 6 | Sat 9 Feb 2019 | 2-1 v Berwick RangersBerwick Rangers 1-2 Stirling Albion | Ladbrokes League Two |
| 7 | Tue 12 Feb 2019 | 1-0 v Albion RoversStirling Albion 1-0 Albion Rovers | Ladbrokes League Two |
| 8 | Sat 16 Feb 2019 | 2-3 v Elgin CityElgin City 3-2 Stirling Albion | Ladbrokes League Two |
| 9 | Sat 23 Feb 2019 | 0-1 v PeterheadStirling Albion 0-1 Peterhead | Ladbrokes League Two |
| 10 | Tue 26 Feb 2019 | 0-1 v ClydeStirling Albion 0-1 Clyde | Ladbrokes League Two |
| 11 | Sat 2 Mar 2019 | 2-1 v CowdenbeathCowdenbeath 1-2 Stirling Albion | Ladbrokes League Two |
| 12 | Sat 9 Mar 2019 | 0-1 v Albion RoversStirling Albion 0-1 Albion Rovers | Ladbrokes League Two |
| 13 | Sat 16 Mar 2019 | 1-3 v ClydeClyde 3-1 Stirling Albion | Ladbrokes League Two |
| 14 | Sat 30 Mar 2019 | 0-0 v Queens ParkQueens Park 0-0 Stirling Albion | Ladbrokes League Two |
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