[10] Stirling 3-1 Annan Athletic [5] 2016-12-17 15:00
Weather: Cold Stadium: Forthbank Stadium Pitch: Good Round: 16
Head to Head
| Scotland League Two | 2016/08/06 14:00 | Annan Athletic v Stirling | L | 3-2 |
| Scotland League Two | 2016/04/23 14:00 | Stirling v Annan Athletic | W | 2-1 |
| Scotland League Two | 2016/02/27 15:00 | Annan Athletic v Stirling | D | 2-2 |
| Scotland League Two | 2015/12/19 15:00 | Stirling v Annan Athletic | W | 1-0 |
| Scotland League Two | 2015/08/15 14:00 | Annan Athletic v Stirling | D | 1-1 |
| Scotland League One Play-Offs | 2014/05/10 14:00 | Annan Athletic v Stirling | W | 3-5 |
| Scotland League One Play-Offs | 2014/05/07 18:45 | Stirling v Annan Athletic | W | 3-1 |