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| Date | Match | Score |
|---|---|---|
| 24.04.2021 | Southend - Leyton Orient | 2 : 1 |
| 29.12.2020 | Leyton Orient - Southend | 2 : 0 |
| 03.09.2019 | Leyton Orient - Southend | 2 : 0 |
| 04.10.2016 | Southend - Leyton Orient | 1 : 0 |
| 20.02.2013 | Southend - Leyton Orient | 2 : 2 |
| 05.02.2013 | Leyton Orient - Southend | 0 : 1 |
| 09.08.2011 | Southend - Leyton Orient | 2 : 2 |
| Date | Match | Score | Res |
|---|---|---|---|
| 15.09.2026 | Southend - Tamworth | 3 - 1 | W |
| 12.09.2026 | Carlisle - Southend | 2 - 2 | D |
| 05.09.2026 | Southend - Yeovil Town | 3 - 2 | W |
| 31.08.2026 | Woking - Southend | 1 - 1 | D |
| 28.08.2026 | Southend - Kidderminster Harriers | 1 - 3 | L |
| Date | Match | Score | Res |
|---|---|---|---|
| 15.09.2026 | Leyton Orient - Arsenal U21 | 1 - 2 | L |
| 12.09.2026 | Leyton Orient - Wycombe | 2 - 3 | L |
| 08.09.2026 | Leyton Orient - Bradford | 1 - 3 | L |
| 05.09.2026 | Luton - Leyton Orient | 1 - 1 | D |
| 01.09.2026 | Bromley - Leyton Orient | 0 - 5 | W |