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 |
Home History
| Club Friendly List | 2024/07/16 18:30 | Canvey Island v Southend | W | 1-2 |
| Club Friendly List | 2024/07/13 13:00 | Great Wakering Rovers v Southend | W | 0-5 |
| England National League | 2024/04/20 11:15 | Southend v Rochdale | L | 1-2 |
| England National League | 2024/04/13 14:00 | AFC Fylde v Southend | W | 0-2 |
| England National League | 2024/04/09 18:45 | Wealdstone v Southend | W | 1-2 |
| England National League | 2024/04/01 14:00 | Southend v Boreham Wood | W | 4-2 |
| England National League | 2024/03/29 15:00 | Ebbsfleet United v Southend | D | 1-1 |
| England National League | 2024/03/26 19:45 | Solihull Moors v Southend | W | 0-3 |
Away History
| Club Friendly List | 2024/07/26 18:30 | Sheppey Utd v Gillingham | D | 1-1 |
| Club Friendly List | 2024/07/23 18:45 | Dartford v Gillingham | W | 0-4 |
| Club Friendly List | 2024/07/20 14:00 | Gillingham v Watford | W | 2-0 |
| Club Friendly List | 2024/07/19 18:45 | Chatham Town v Gillingham | L | 2-1 |
| Club Friendly List | 2024/07/13 12:00 | Gillingham v Millwall | D | 0-0 |
| England League 2 | 2024/04/27 14:00 | Gillingham v Doncaster | D | 2-2 |
| England League 2 | 2024/04/20 14:00 | Mansfield v Gillingham | L | 2-1 |
| England League 2 | 2024/04/13 14:00 | Gillingham v Barrow | W | 3-0 |