Head to Head
| 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 | 2019/08/31 14:00 | Salford City v Leyton Orient | D | 1-1 |
| England League 2 | 2019/08/24 14:00 | Leyton Orient v Crawley Town | L | 2-3 |
| England League 2 | 2019/08/20 18:45 | Mansfield v Leyton Orient | W | 2-3 |
| England League 2 | 2019/08/17 14:00 | Leyton Orient v Stevenage | D | 0-0 |
| England EFL Cup | 2019/08/13 18:45 | Plymouth v Leyton Orient | L | 2-0 |
| England League 2 | 2019/08/10 14:00 | Macclesfield v Leyton Orient | L | 3-0 |
| England League 2 | 2019/08/03 14:00 | Leyton Orient v Cheltenham | W | 1-0 |
| Club Friendly List | 2019/07/27 14:00 | Leyton Orient v Norwich U23 | W | 2-1 |
Away History
| England League 1 | 2019/08/31 14:00 | Southend v Rochdale | L | 0-3 |
| England EFL Cup | 2019/08/27 18:45 | Southend v Milton Keynes Dons | L | 1-4 |
| England League 1 | 2019/08/24 14:00 | Wycombe v Southend | L | 4-3 |
| England League 1 | 2019/08/20 18:45 | Southend v Peterborough | L | 0-2 |
| England League 1 | 2019/08/17 14:00 | Lincoln City v Southend | L | 4-0 |
| England EFL Cup | 2019/08/13 18:45 | Stevenage v Southend | W | 1-2 |
| England League 1 | 2019/08/10 14:00 | Southend v Blackpool | L | 1-3 |
| England League 1 | 2019/08/03 14:00 | Coventry v Southend | L | 1-0 |