[23] Southend 2-1 Leyton Orient [10] 2021-04-24 14:00
Stadium: Roots Hall Round: 44
Referee: Trevor Kettle Home Manager: Phil Brown Away Manager: Joel Joshua Frederick McAnuff
Head to Head
| England League 2 | 2020/12/29 19:00 | Leyton Orient v Southend | L | 2-0 |
| England EFL Trophy | 2019/09/03 18:45 | Leyton Orient v Southend | L | 2-0 |
| Club Friendly List | 2018/07/28 14:00 | Leyton Orient v Southend | D | 2-2 |
| England EFL Trophy | 2016/10/04 18:45 | Southend v Leyton Orient | W | 1-0 |
| Club Friendly List | 2015/08/02 12:00 | Southend v Leyton Orient | L | 0-1 |