Head to Head
| Club Friendly List | 2022/07/23 14:00 | Southend v Gillingham | L | 0-1 |
| England EFL Cup | 2020/09/05 12:00 | Gillingham v Southend | L | 1-0 |
| England League 1 | 2020/02/18 19:45 | Southend v Gillingham | L | 0-1 |
| England League 1 | 2019/10/05 14:00 | Gillingham v Southend | L | 3-1 |
| Club Friendly List | 2019/07/26 18:00 | Gillingham v Southend | D | 1-1 |
| England League 1 | 2019/01/01 15:00 | Southend v Gillingham | W | 2-0 |
| England League 1 | 2018/10/13 14:00 | Gillingham v Southend | W | 0-2 |
| England League 1 | 2018/04/02 14:00 | Southend v Gillingham | W | 4-0 |
| England EFL Trophy | 2017/08/29 18:45 | Gillingham v Southend | L | 2-1 |
| England League 1 | 2017/08/26 14:00 | Gillingham v Southend | D | 3-3 |
| England League 1 | 2017/02/25 15:00 | Gillingham v Southend | L | 2-1 |
| England EFL Cup | 2016/08/09 18:45 | Southend v Gillingham | L | 1-3 |
| England League 1 | 2016/08/06 14:00 | Southend v Gillingham | L | 1-3 |
| England League 1 | 2016/03/19 15:00 | Southend v Gillingham | D | 1-1 |
| England League 1 | 2015/10/24 14:00 | Gillingham v Southend | D | 1-1 |