1 | Sat 8 Sep 2018 | 0-3 v ArbroathArbroath 3-0 Annan Athletic | IRN-BRU Cup Second Round |
2 | Sat 24 Nov 2018 | 0-0 v MontroseMontrose 0-0 Annan Athletic | William Hill Scottish Cup Third Round |
3 | Sat 22 Dec 2018 | 4-0 v Berwick RangersAnnan Athletic 4-0 Berwick Rangers | Ladbrokes League Two |
4 | Sat 29 Dec 2018 | 1-1 v Albion RoversAlbion Rovers 1-1 Annan Athletic | Ladbrokes League Two |
5 | Sat 5 Jan 2019 | 2-0 v Elgin CityAnnan Athletic 2-0 Elgin City | Ladbrokes League Two |
6 | Sat 12 Jan 2019 | 1-2 v Stirling AlbionStirling Albion 2-1 Annan Athletic | Ladbrokes League Two |
7 | Sat 26 Jan 2019 | 3-0 v PeterheadAnnan Athletic 3-0 Peterhead | Ladbrokes League Two |
8 | Sat 9 Feb 2019 | 1-1 v ClydeAnnan Athletic 1-1 Clyde | Ladbrokes League Two |
9 | Sat 16 Feb 2019 | 4-2 v CowdenbeathCowdenbeath 2-4 Annan Athletic | Ladbrokes League Two |
10 | Sat 23 Feb 2019 | 4-0 v Albion RoversAnnan Athletic 4-0 Albion Rovers | Ladbrokes League Two |
11 | Tue 26 Feb 2019 | 2-1 v Berwick RangersBerwick Rangers 1-2 Annan Athletic | Ladbrokes League Two |
12 | Sat 4 May 2019 | 2-0 v Albion RoversAlbion Rovers 0-2 Annan Athletic | Ladbrokes League Two |