| 1 | 17/7/2018 | 4-0 v Berwick RangersAnnan Athletic 4-0 Berwick Rangers | Betfred Cup Group F |
| 2 | 21/7/2018 | 0-1 v LivingstonLivingston 1-0 Annan Athletic | Betfred Cup Group F |
| 3 | 24/7/2018 | 1-4 v AirdrieoniansAirdrieonians 4-1 Annan Athletic | Betfred Cup Group F |
| 4 | 20/10/2018 | 1-0 v RothesRothes 0-1 Annan Athletic | William Hill Scottish Cup Second Round |
| 5 | 24/11/2018 | 0-0 v MontroseMontrose 0-0 Annan Athletic | William Hill Scottish Cup Third Round |
| 6 | 27/11/2018 | 3-4 v MontroseAnnan Athletic 3-4 Montrose | William Hill Scottish Cup Third Round Replay |
| 7 | 22/12/2018 | 4-0 v Berwick RangersAnnan Athletic 4-0 Berwick Rangers | Ladbrokes League Two |
| 8 | 29/12/2018 | 1-1 v Albion RoversAlbion Rovers 1-1 Annan Athletic | Ladbrokes League Two |
| 9 | 19/1/2019 | 2-1 v Edinburgh CityEdinburgh City 1-2 Annan Athletic | Ladbrokes League Two |
| 10 | 26/1/2019 | 3-0 v PeterheadAnnan Athletic 3-0 Peterhead | Ladbrokes League Two |
| 11 | 9/2/2019 | 1-1 v ClydeAnnan Athletic 1-1 Clyde | Ladbrokes League Two |
| 12 | 16/2/2019 | 4-2 v CowdenbeathCowdenbeath 2-4 Annan Athletic | Ladbrokes League Two |
| 13 | 23/2/2019 | 4-0 v Albion RoversAnnan Athletic 4-0 Albion Rovers | Ladbrokes League Two |
| 14 | 2/3/2019 | 2-1 v Queens ParkAnnan Athletic 2-1 Queens Park | Ladbrokes League Two |
| 15 | 9/3/2019 | 1-2 v PeterheadPeterhead 2-1 Annan Athletic | Ladbrokes League Two |
| 16 | 16/3/2019 | 3-1 v Edinburgh CityAnnan Athletic 3-1 Edinburgh City | Ladbrokes League Two |
| 17 | 23/3/2019 | 1-2 v ClydeClyde 2-1 Annan Athletic | Ladbrokes League Two |
| 18 | 30/3/2019 | 1-0 v Elgin CityElgin City 0-1 Annan Athletic | Ladbrokes League Two |
| 19 | 6/4/2019 | 6-0 v Berwick RangersAnnan Athletic 6-0 Berwick Rangers | Ladbrokes League Two |
| 20 | 13/4/2019 | 2-2 v Stirling AlbionAnnan Athletic 2-2 Stirling Albion | Ladbrokes League Two |
| 21 | 20/4/2019 | 3-0 v Queens ParkQueens Park 0-3 Annan Athletic | Ladbrokes League Two |
| 22 | 27/4/2019 | 3-2 v CowdenbeathAnnan Athletic 3-2 Cowdenbeath | Ladbrokes League Two |
| 23 | 4/5/2019 | 2-0 v Albion RoversAlbion Rovers 0-2 Annan Athletic | Ladbrokes League Two |
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