[12] Leyton Orient 2-0 Kerasan Prishtina [23] 2020-11-17 07:00
Stadium: Matchroom Stadium Round: 21
Referee: Craig Hicks Home Manager: Ross Embleton Away Manager: Mark Molesley
Head to Head
| England EFL Trophy | 2019/09/03 18:45 | Leyton Orient v Southend | W | 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 | L | 1-0 |
| Club Friendly List | 2015/08/02 12:00 | Southend v Leyton Orient | W | 0-1 |
Home History
| England League 2 | 2020/11/14 15:00 | Colchester v Leyton Orient | L | 2-1 |
| England EFL Trophy | 2020/11/10 19:00 | Charlton v Leyton Orient | L | 3-1 |
| England FA Cup | 2020/11/07 15:00 | Leyton Orient v Newport County | L | 1-2 |
| England League 2 | 2020/11/03 19:00 | Forest Green v Leyton Orient | L | 2-1 |
| England League 2 | 2020/10/31 15:00 | Leyton Orient v Bolton | W | 4-0 |
| England League 2 | 2020/10/27 19:00 | Leyton Orient v Exeter | D | 1-1 |
| England League 2 | 2020/10/24 14:00 | Stevenage v Leyton Orient | W | 0-2 |
| England League 2 | 2020/10/20 18:00 | Tranmere v Leyton Orient | W | 0-1 |
Away History
| England League 2 | 2020/11/14 15:00 | Walsall v Southend | W | 0-1 |
| England EFL Trophy | 2020/11/10 19:00 | Colchester v Southend | L | 6-1 |
| England FA Cup | 2020/11/07 15:00 | Boreham Wood v Southend | L | 7-6 |
| England League 2 | 2020/11/03 19:00 | Bradford v Southend | L | 3-0 |
| England League 2 | 2020/10/31 15:00 | Southend v Port Vale | L | 0-2 |
| England League 2 | 2020/10/27 19:00 | Southend v Oldham | L | 1-2 |
| England League 2 | 2020/10/24 14:00 | Tranmere v Southend | L | 2-0 |
| England League 2 | 2020/10/20 18:45 | Salford City v Southend | L | 3-0 |