| 1 | 22/12/2018 | 4-0 v Berwick RangersAnnan Athletic 4-0 Berwick Rangers | Ladbrokes League Two |
| 2 | 29/12/2018 | 1-1 v Albion RoversAlbion Rovers 1-1 Annan Athletic | Ladbrokes League Two |
| 3 | 16/2/2019 | 4-2 v CowdenbeathCowdenbeath 2-4 Annan Athletic | Ladbrokes League Two |
| 4 | 23/2/2019 | 4-0 v Albion RoversAnnan Athletic 4-0 Albion Rovers | Ladbrokes League Two |
| 5 | 26/2/2019 | 2-1 v Berwick RangersBerwick Rangers 1-2 Annan Athletic | Ladbrokes League Two |
| 6 | 2/3/2019 | 2-1 v Queens ParkAnnan Athletic 2-1 Queens Park | Ladbrokes League Two |
| 7 | 9/3/2019 | 1-2 v PeterheadPeterhead 2-1 Annan Athletic | Ladbrokes League Two |
| 8 | 16/3/2019 | 3-1 v Edinburgh CityAnnan Athletic 3-1 Edinburgh City | Ladbrokes League Two |
| 9 | 23/3/2019 | 1-2 v ClydeClyde 2-1 Annan Athletic | Ladbrokes League Two |
| 10 | 6/4/2019 | 6-0 v Berwick RangersAnnan Athletic 6-0 Berwick Rangers | Ladbrokes League Two |
| 11 | 13/4/2019 | 2-2 v Stirling AlbionAnnan Athletic 2-2 Stirling Albion | Ladbrokes League Two |
| 12 | 27/4/2019 | 3-2 v CowdenbeathAnnan Athletic 3-2 Cowdenbeath | Ladbrokes League Two |
| 13 | 4/5/2019 | 2-0 v Albion RoversAlbion Rovers 0-2 Annan Athletic | Ladbrokes League Two |
