[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 |
Home History
| Scotland League Two | 2019/11/16 15:00 | FC Edinburgh v Albion | W | 3-2 |
| Scotland League Two | 2019/11/09 15:00 | FC Edinburgh v Elgin | D | 1-1 |
| Scotland League Two | 2019/11/02 15:00 | Brechin v FC Edinburgh | W | 2-3 |
| Scotland League Two | 2019/10/29 19:45 | FC Edinburgh v Stenhousemuir | W | 4-0 |
| Scotland FA Cup | 2019/10/18 18:30 | FC Edinburgh v Banks O'Dee | W | 3-1 |
| Scotland League Two | 2019/10/05 14:00 | Cowdenbeath v FC Edinburgh | L | 1-0 |
| Scotland League Two | 2019/09/28 14:00 | FC Edinburgh v Queen's Park | W | 2-1 |
| Scotland League Two | 2019/09/21 14:00 | Albion v FC Edinburgh | W | 1-3 |
Away History
| Scotland League Two | 2019/11/16 15:00 | Stirling v Annan Athletic | L | 2-0 |
| 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 |