[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 |
Home History
| Scotland League Two | 2016/12/10 15:00 | FC Edinburgh v Stirling | L | 2-0 |
| Scotland League Two | 2016/12/06 19:45 | Berwick Rangers v Stirling | L | 3-2 |
| Scotland FA Cup | 2016/12/03 15:00 | Stirling v Wick Academy | W | 2-0 |
| Scotland League Two | 2016/11/19 15:00 | Stirling v Arbroath | D | 2-2 |
| Scotland League Two | 2016/11/12 15:00 | Elgin v Stirling | W | 2-3 |
| Scotland League Two | 2016/11/05 15:00 | Stirling v Forfar | L | 0-3 |
| Scotland League Two | 2016/10/29 14:00 | Clyde v Stirling | D | 1-1 |
| Scotland FA Cup | 2016/10/22 14:00 | Linlithgow Rose v Stirling | W | 0-3 |
Away History
| Scotland League Two | 2016/12/13 19:45 | Forfar v Annan Athletic | L | 5-1 |
| Scotland League Two | 2016/12/10 15:00 | Annan Athletic v Cowdenbeath | W | 2-0 |
| Scotland FA Cup | 2016/12/03 15:00 | Formartine United v Annan Athletic | L | 4-0 |
| Scotland League Two | 2016/11/19 15:00 | Annan Athletic v Elgin | W | 1-0 |
| Scotland League Two | 2016/11/12 15:00 | FC Edinburgh v Annan Athletic | L | 1-0 |
| Scotland League Two | 2016/11/08 19:45 | Annan Athletic v Montrose | L | 2-3 |
| Scotland League Two | 2016/11/05 15:00 | Annan Athletic v Arbroath | L | 1-2 |
| Scotland FA Cup | 2016/10/29 14:00 | East Stirlingshire v Annan Athletic | W | 1-2 |