| 17 Oct 20 | r01  | CowdenbeathCowdenbeath | 0 - 3 | Annan AthleticAnnan Athleti |
| |
| 24 Oct 20 | r02 | Annan AthleticAnnan Athleti | 1 - 1 | StranraerStranraer |
| |
| 31 Oct 20 | r03 | Stirling AlbionStirling Albi | 1 - 0 | Annan AthleticAnnan Athleti |
| |
| 07 Nov 20 | r04 | Annan AthleticAnnan Athleti | 2 - 3 | Albion RoversAlbion Rovers |
| |
| 21 Nov 20 | r05 | StenhousemuirStenhousemuir | 1 - 2 | Annan AthleticAnnan Athleti |
| |
| 28 Nov 20 | r06 | Annan AthleticAnnan Athleti | 0 - 4 | Edinburgh CityEdinburgh Cit |
| |
| 05 Dec 20 | r07 | Elgin CityElgin City | 1 - 0 | Annan AthleticAnnan Athleti |
| |
| 19 Dec 20 | r09 | Annan AthleticAnnan Athleti | 1 - 2 | Queens ParkQueens Park |
| |
| 22 Dec 20 | r08 | Brechin CityBrechin City | 0 - 0 | Annan AthleticAnnan Athleti |
| |
| 02 Jan 21 | r10 | StranraerStranraer | 2 - 0 | Annan AthleticAnnan Athleti |
| |
| 13 Mar 21 | r19 | Elgin CityElgin City | - | Annan AthleticAnnan Athleti |
| |
| 20 Mar 21 | r11 | Annan AthleticAnnan Athleti | 0 - 0 | CowdenbeathCowdenbeath |
| |
| 20 Mar 21 | r20 | Annan AthleticAnnan Athleti | - | Albion RoversAlbion Rovers |
| |
| 27 Mar 21 | r12 | Albion RoversAlbion Rovers | 1 - 1 | Annan AthleticAnnan Athleti |
| |
| 27 Mar 21 | r21 | Stirling AlbionStirling Albi | - | Annan AthleticAnnan Athleti |
| |
| 03 Apr 21 | r13 | Annan AthleticAnnan Athleti | 0 - 3 | Elgin CityElgin City |
| |
| 03 Apr 21 | r22 | CowdenbeathCowdenbeath | - | Annan AthleticAnnan Athleti |
| |
| 06 Apr 21 | r14 | Edinburgh CityEdinburgh Cit | 1 - 1 | Annan AthleticAnnan Athleti |
| |
| 10 Apr 21 | r15 | Annan AthleticAnnan Athleti | 1 - 2 | Stirling AlbionStirling Albi |
| |
| 10 Apr 21 | r23 | Annan AthleticAnnan Athleti | - | Edinburgh CityEdinburgh Cit |
| |
| 13 Apr 21 | r16 | Queens ParkQueens Park | 1 - 0 | Annan AthleticAnnan Athleti |
| |
| 17 Apr 21 | r17 | Annan AthleticAnnan Athleti | 3 - 0 | Brechin CityBrechin City |
| |
| 17 Apr 21 | r24 | Annan AthleticAnnan Athleti | - | StranraerStranraer |
| |
| 20 Apr 21 | r25 | StenhousemuirStenhousemuir | - | Annan AthleticAnnan Athleti |
| |
| 20 Apr 21 | r18 | Annan AthleticAnnan Athleti | 5 - 1 | StenhousemuirStenhousemuir |
| |
| 24 Apr 21 | r26 | Brechin CityBrechin City | - | Annan AthleticAnnan Athleti |
| |
| 24 Apr 21 | r01 | Albion RoversAlbion Rovers | 1 - 0 | Annan AthleticAnnan Athleti |
| |
| 27 Apr 21 | r02 | Annan AthleticAnnan Athleti | 1 - 1 | StenhousemuirStenhousemuir |
| |
| 29 Apr 21 | r03 | Brechin CityBrechin City | 0 - 3 | Annan AthleticAnnan Athleti |
| |
| 01 May 21 | r04 | Annan AthleticAnnan Athleti | 1 - 1 | CowdenbeathCowdenbeath |
| |
| 01 May 21 | r27 | Annan AthleticAnnan Athleti | - | Queens ParkQueens Park |
Team 2020-2021 Schedules
Annan Athletic
Clyde
Dumbarton
Edinburgh City
Elgin City
Forfar Athletic
Kelty Hearts
Stirling Albion
Stranraer
The Spartans
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