[12] Leyton Orient 2-0 Southend [23] 2020-12-29 19:00
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 | 2020/12/26 13:00 | Cambridge Utd v Leyton Orient | L | 2-1 |
| England League 2 | 2020/12/19 15:00 | Leyton Orient v Crawley Town | L | 1-2 |
| England League 2 | 2020/12/15 18:30 | Morecambe v Leyton Orient | L | 2-1 |
| England League 2 | 2020/12/12 15:00 | Leyton Orient v Newport County | W | 2-1 |
| England EFL Trophy | 2020/12/08 19:00 | Leyton Orient v Bristol Rovers | L | 1-2 |
| England League 2 | 2020/12/05 13:00 | Scunthorpe v Leyton Orient | L | 2-0 |
| England League 2 | 2020/11/28 13:00 | Port Vale v Leyton Orient | W | 2-3 |
| England League 2 | 2020/11/24 19:00 | Leyton Orient v Bradford | W | 1-0 |
Away History
| England League 2 | 2020/12/26 13:00 | Southend v Colchester | W | 2-0 |
| England League 2 | 2020/12/19 15:00 | Mansfield v Southend | D | 1-1 |
| England League 2 | 2020/12/15 19:45 | Southend v Grimsby | W | 3-1 |
| England League 2 | 2020/12/12 15:00 | Southend v Scunthorpe | W | 1-0 |
| England League 2 | 2020/12/05 15:00 | Stevenage v Southend | D | 0-0 |
| England League 2 | 2020/11/28 15:00 | Bolton v Southend | L | 3-0 |
| England League 2 | 2020/11/24 19:00 | Southend v Forest Green | L | 0-1 |
| England League 2 | 2020/11/14 15:00 | Walsall v Southend | W | 0-1 |