Head to Head
| Scotland League Two | 2019/09/21 14:00 | Annan Athletic v Stirling | D | 0-0 |
| Scotland League Two | 2019/04/13 14:00 | Annan Athletic v Stirling | D | 2-2 |
| Scotland League Two | 2019/01/12 15:00 | Stirling v Annan Athletic | W | 2-1 |
| Scotland League Two | 2018/11/17 15:00 | Annan Athletic v Stirling | D | 2-2 |
| Scotland League Two | 2018/09/22 14:00 | Stirling v Annan Athletic | L | 1-2 |
| Scotland League Two | 2018/04/21 14:00 | Annan Athletic v Stirling | L | 3-1 |
| Scotland League Two | 2018/02/17 15:00 | Stirling v Annan Athletic | W | 3-0 |
| Scotland League Two | 2017/12/16 15:00 | Annan Athletic v Stirling | D | 1-1 |
Home History
| Scotland League Two | 2019/11/09 15:00 | Cove Rangers v Stirling | L | 1-0 |
| Scotland League Two | 2019/11/02 15:00 | Stirling v Albion | W | 3-0 |
| Scotland League Two | 2019/10/29 19:45 | Stirling v Cowdenbeath | D | 0-0 |
| Scotland FA Cup | 2019/10/19 14:00 | Stirling v Strathspey Thistle | W | 2-0 |
| Scotland League Two | 2019/10/05 14:00 | Brechin v Stirling | D | 1-1 |
| Scotland League Two | 2019/09/28 14:00 | Stirling v Stenhousemuir | D | 1-1 |
| Scotland League Two | 2019/09/21 14:00 | Annan Athletic v Stirling | D | 0-0 |
| Scotland League Two | 2019/09/14 14:00 | Stirling v Elgin | W | 1-0 |
Away History
| Scotland League Two | 2019/11/12 19:45 | Annan Athletic v Brechin | W | 5-2 |
| Scotland League Two | 2019/11/09 15:00 | Annan Athletic v Cowdenbeath | W | 1-0 |
| Scotland League Two | 2019/11/02 15:00 | Elgin v Annan Athletic | L | 4-0 |
| Scotland FA Cup | 2019/10/26 14:00 | Brechin v Annan Athletic | W | 0-2 |
| Scotland FA Cup | 2019/10/19 14:00 | Annan Athletic v Brechin | D | 2-2 |
| Scotland League Two | 2019/10/05 14:00 | Queen's Park v Annan Athletic | W | 1-2 |
| Scotland League Two | 2019/09/28 14:00 | Cove Rangers v Annan Athletic | L | 3-0 |
| Scotland League Two | 2019/09/21 14:00 | Annan Athletic v Stirling | D | 0-0 |