| 1 | Sat 16 Nov 2019 | 0-2 v Stirling AlbionStirling Albion 2-0 Annan Athletic | Ladbrokes League Two |
| 2 | Sat 28 Dec 2019 | 3-2 v Queens ParkAnnan Athletic 3-2 Queens Park | Ladbrokes League Two |
| 3 | Sat 4 Jan 2020 | 1-3 v CowdenbeathCowdenbeath 3-1 Annan Athletic | Ladbrokes League Two |
| 4 | Sat 11 Jan 2020 | 0-4 v Elgin CityAnnan Athletic 0-4 Elgin City | Ladbrokes League Two |
| 5 | Sat 18 Jan 2020 | 2-3 v Stirling AlbionAnnan Athletic 2-3 Stirling Albion | Ladbrokes League Two |
| 6 | Sat 25 Jan 2020 | 0-2 v Cove RangersCove Rangers 2-0 Annan Athletic | Ladbrokes League Two |
| 7 | Sat 8 Feb 2020 | 0-3 v Elgin CityElgin City 3-0 Cove Rangers | Ladbrokes League Two |
| 8 | Sat 15 Feb 2020 | 2-1 v Edinburgh CityCove Rangers 2-1 Edinburgh City | Ladbrokes League Two |
| 9 | Sat 22 Feb 2020 | 2-0 v Queens ParkCove Rangers 2-0 Queens Park | Ladbrokes League Two |
| 10 | Sat 29 Feb 2020 | 3-0 v StenhousemuirStenhousemuir 0-3 Cove Rangers | Ladbrokes League Two |
| 11 | Sat 7 Mar 2020 | 3-2 v Brechin CityCove Rangers 3-2 Brechin City | Ladbrokes League Two |
| 12 | Tue 10 Mar 2020 | 7-1 v Stirling AlbionStirling Albion 1-7 Cove Rangers | Ladbrokes League Two |
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