Head to Head
| 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 |
Home History
| England National League | 2022/05/15 14:00 | Southend v Torquay | D | 1-1 |
| England National League | 2022/05/02 14:00 | Southend v Weymouth | D | 1-1 |
| England National League | 2022/04/30 14:00 | Wrexham v Southend | L | 1-0 |
| England National League | 2022/04/26 18:45 | Southend v Boreham Wood | W | 1-0 |
| England National League | 2022/04/23 14:00 | Southend v Halifax | W | 1-0 |
| England National League | 2022/04/18 14:00 | Barnet v Southend | W | 1-3 |
| England National League | 2022/04/15 14:00 | Southend v Wealdstone | L | 0-1 |
| England National League | 2022/04/09 16:20 | Stockport v Southend | L | 5-0 |
Away History
| England League 1 | 2022/04/30 11:30 | Gillingham v Rotherham | L | 0-2 |
| England League 1 | 2022/04/23 14:00 | Portsmouth v Gillingham | L | 3-1 |
| England League 1 | 2022/04/18 14:00 | Gillingham v Fleetwood Town | D | 0-0 |
| England League 1 | 2022/04/15 14:00 | Cheltenham v Gillingham | D | 2-2 |
| England League 1 | 2022/04/09 14:00 | Gillingham v Wycombe | D | 1-1 |
| England League 1 | 2022/04/02 14:00 | Sunderland v Gillingham | L | 1-0 |
| England League 1 | 2022/03/26 15:00 | Accrington Stanley v Gillingham | W | 1-2 |
| England League 1 | 2022/03/19 15:00 | Gillingham v Sheff Wed | D | 0-0 |