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