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 | Annan Athletic |
| 04/05/19 16:00 | Albion Rovers - : - Annan Athletic |
| 27/04/19 16:00 | Annan Athletic - : - Cowdenbeath |
| 20/04/19 16:00 | Queen\'s Park FC - : - Annan Athletic |
| 13/04/19 16:00 | Annan Athletic - : - Stirling Albion |
| 06/04/19 16:00 | Annan Athletic - : - Berwick Rangers |
| 30/03/19 16:00 | Elgin City - : - Annan Athletic |
| 23/03/19 16:00 | Clyde - : - Annan Athletic |
| 16/03/19 16:00 | Annan Athletic - : - Edinburgh City |
| 09/03/19 16:00 | Peterhead - : - Annan Athletic |
| 02/03/19 16:00 | Annan Athletic - : - Queen\'s Park FC |
| 26/02/19 20:45 | Berwick Rangers - : - Annan Athletic |  |
| 23/02/19 16:00 | Annan Athletic 4 : 0 Albion Rovers | |
| 16/02/19 16:00 | Cowdenbeath 2 : 4 Annan Athletic | |
| 09/02/19 16:00 | Annan Athletic 1 : 1 Clyde | |
| 26/01/19 16:00 | Annan Athletic 3 : 0 Peterhead | |
| 19/01/19 16:00 | Edinburgh City 1 : 2 Annan Athletic | |
| 12/01/19 16:00 | Stirling Albion 2 : 1 Annan Athletic | |
| 05/01/19 16:00 | Annan Athletic 2 : 0 Elgin City | |
| 29/12/18 16:00 | Albion Rovers 1 : 1 Annan Athletic | |
| 22/12/18 16:00 | Annan Athletic 4 : 0 Berwick Rangers | |
| 15/12/18 16:00 | Clyde 1 : 0 Annan Athletic | |
| 08/12/18 16:00 | Annan Athletic 1 : 2 Edinburgh City | |
| 01/12/18 16:00 | Peterhead 2 : 1 Annan Athletic | |
| 27/11/18 20:45 | Annan Athletic 3 : 4 Montrose |
| 24/11/18 16:00 | Montrose 0 : 0 Annan Athletic |
| 17/11/18 16:00 | Annan Athletic 2 : 2 Stirling Albion | |
| 10/11/18 16:00 | Annan Athletic 0 : 2 Cowdenbeath | |
| 03/11/18 16:00 | Queen\'s Park FC 0 : 0 Annan Athletic | |
| 27/10/18 16:00 | Elgin City 0 : 1 Annan Athletic | |
| 20/10/18 16:00 | Rothes FC 0 : 1 Annan Athletic |
| 06/10/18 16:00 | Annan Athletic 3 : 1 Albion Rovers | |
| 29/09/18 16:00 | Annan Athletic 1 : 3 Peterhead | |
| 22/09/18 16:00 | Stirling Albion 1 : 2 Annan Athletic | |
| 15/09/18 16:00 | Edinburgh City 2 : 1 Annan Athletic | |
| 08/09/18 16:00 | Arbroath 3 : 0 Annan Athletic |
| 01/09/18 16:00 | Annan Athletic 1 : 2 Clyde | |
| 25/08/18 16:00 | Berwick Rangers 0 : 3 Annan Athletic | |
| 18/08/18 16:00 | Annan Athletic 3 : 1 Queen\'s Park FC | |
| 14/08/18 20:45 | Annan Athletic 4 : 0 Celtic U20 |
| 11/08/18 16:00 | Cowdenbeath 1 : 2 Annan Athletic | |
| 04/08/18 16:00 | Annan Athletic 1 : 1 Elgin City | |
| 24/07/18 20:45 | Airdrieonians 4 : 1 Annan Athletic | |
| 21/07/18 16:00 | Livingston 1 : 0 Annan Athletic | |
| 17/07/18 20:45 | Annan Athletic 4 : 0 Berwick Rangers | |
| 14/07/18 16:00 | Annan Athletic 1 : 0 Hamilton | |
| 03/07/18 20:30 | Gretna FC 2 : 3 Annan Athletic |
| 30/06/18 15:00 | Annan Athletic 2 : 2 Queen of the South |
| 28/04/18 16:00 | Cowdenbeath 0 : 2 Annan Athletic | |
| 21/04/18 16:00 | Annan Athletic 3 : 1 Stirling Albion | |
| 14/04/18 16:00 | Stenhousemuir 3 : 2 Annan Athletic | |
| 07/04/18 16:00 | Annan Athletic 4 : 1 Elgin City | |
| 31/03/18 16:00 | Annan Athletic 0 : 0 Berwick Rangers | |
| 24/03/18 16:00 | Peterhead 1 : 0 Annan Athletic | |
| 17/03/18 16:00 | Annan Athletic 1 : 1 Clyde | |
| 13/03/18 20:45 | Montrose 2 : 1 Annan Athletic | |
| 10/03/18 16:00 | Annan Athletic 2 : 3 Edinburgh City | |
| 24/02/18 16:00 | Annan Athletic 2 : 0 Stenhousemuir | |
| 20/02/18 20:45 | Annan Athletic 3 : 3 Peterhead | |
| 17/02/18 16:00 | Stirling Albion 3 : 0 Annan Athletic | |
| 10/02/18 16:00 | Elgin City 2 : 1 Annan Athletic | |
| 03/02/18 16:00 | Annan Athletic 1 : 1 Cowdenbeath | |
| 27/01/18 16:00 | Edinburgh City 3 : 2 Annan Athletic | |
| 13/01/18 16:00 | Berwick Rangers 0 : 2 Annan Athletic | |
| 06/01/18 16:00 | Annan Athletic 0 : 1 Montrose | |
| 02/01/18 16:00 | Clyde 0 : 0 Annan Athletic | |
| 23/12/17 16:00 | Annan Athletic 2 : 1 Edinburgh City | |
| 16/12/17 16:00 | Annan Athletic 1 : 1 Stirling Albion | |
| 09/12/17 16:00 | Stenhousemuir 1 : 3 Annan Athletic | |
| 02/12/17 16:00 | Annan Athletic 2 : 0 Elgin City | |
| 25/11/17 16:00 | Annan Athletic 0 : 0 Clyde | |
| 18/11/17 16:00 | Cowdenbeath 1 : 1 Annan Athletic | |
| 11/11/17 16:00 | Montrose 1 : 1 Annan Athletic | |
| 04/11/17 16:00 | Annan Athletic 0 : 0 Berwick Rangers | |
| 28/10/17 16:00 | Peterhead 1 : 0 Annan Athletic | |
| 21/10/17 16:00 | Edinburgh City 0 : 1 Annan Athletic | |
| 14/10/17 16:00 | Berwick Rangers 1 : 0 Annan Athletic |
| 30/09/17 16:00 | Annan Athletic 1 : 0 Cowdenbeath | |
| 23/09/17 16:00 | Stirling Albion 3 : 2 Annan Athletic | |
| 16/09/17 16:00 | Annan Athletic 1 : 1 Stenhousemuir | |
| 09/09/17 16:00 | Elgin City 0 : 1 Annan Athletic | |
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