| 1 | Tue 13 Aug 2019 | 2-0 v East FifeEast Fife 0-2 Stirling Albion | Tunnock's Challenge Cup Second Round |
| 2 | Sat 17 Aug 2019 | 0-1 v Edinburgh CityEdinburgh City 1-0 Stirling Albion | Ladbrokes League Two |
| 3 | Sat 24 Aug 2019 | 1-2 v Cove RangersStirling Albion 1-2 Cove Rangers | Ladbrokes League Two |
| 4 | Sat 31 Aug 2019 | 1-2 v Albion RoversAlbion Rovers 2-1 Stirling Albion | Ladbrokes League Two |
| 5 | Sat 5 Oct 2019 | 1-1 v Brechin CityBrechin City 1-1 Stirling Albion | Ladbrokes League Two |
| 6 | Tue 29 Oct 2019 | 0-0 v CowdenbeathStirling Albion 0-0 Cowdenbeath | Ladbrokes League Two |
| 7 | Sat 2 Nov 2019 | 3-0 v Albion RoversStirling Albion 3-0 Albion Rovers | Ladbrokes League Two |
| 8 | Sat 9 Nov 2019 | 0-1 v Cove RangersCove Rangers 1-0 Stirling Albion | Ladbrokes League Two |
| 9 | Sat 16 Nov 2019 | 2-0 v Annan AthleticStirling Albion 2-0 Annan Athletic | Ladbrokes League Two |
| 10 | Sat 30 Nov 2019 | 2-1 v Elgin CityElgin City 1-2 Stirling Albion | Ladbrokes League Two |
| 11 | Sat 7 Dec 2019 | 2-4 v Brechin CityStirling Albion 2-4 Brechin City | Ladbrokes League Two |
| 12 | Sat 14 Dec 2019 | 1-1 v Queens ParkQueens Park 1-1 Stirling Albion | Ladbrokes League Two |
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