[2] Edinburgh City 4-3 Annan Athletic [4] 2019-11-23 15:00
Stadium: Meadowbank Stadium Round: 9
Home Manager: James McDonaugh Away Manager: Peter Murphy
Head to Head
| Scotland League Two | 2019/09/14 14:00 | FC Edinburgh v Annan Athletic | W | 4-0 |
| Scotland League Two | 2019/03/16 15:00 | Annan Athletic v FC Edinburgh | L | 3-1 |
| Scotland League Two | 2019/01/19 15:00 | FC Edinburgh v Annan Athletic | L | 1-2 |
| Scotland League Two | 2018/12/08 15:00 | Annan Athletic v FC Edinburgh | W | 1-2 |
| Scotland League Two | 2018/09/15 14:00 | FC Edinburgh v Annan Athletic | W | 2-1 |
| Scotland League Two | 2018/03/10 15:00 | Annan Athletic v FC Edinburgh | W | 2-3 |
| Scotland League Two | 2018/01/27 15:00 | FC Edinburgh v Annan Athletic | W | 3-2 |
| Scotland League Two | 2017/12/23 15:00 | Annan Athletic v FC Edinburgh | L | 2-1 |
| Scotland League Two | 2017/10/21 14:00 | FC Edinburgh v Annan Athletic | L | 0-1 |
| Scotland League Two | 2017/04/22 14:00 | FC Edinburgh v Annan Athletic | W | 2-0 |
| Scotland League Two | 2017/02/11 15:00 | Annan Athletic v FC Edinburgh | L | 1-0 |
| Scotland League Two | 2016/11/12 15:00 | FC Edinburgh v Annan Athletic | W | 1-0 |
| Scotland League Two | 2016/09/24 14:00 | Annan Athletic v FC Edinburgh | D | 1-1 |