[1] Portsmouth 0-3 Leyton Orient [12] 2023-09-04 09:00
Stadium: Fratton Park Round: 28
Referee: Ben Speedie Home Manager: John Mousinho Away Manager: Richie Wellens
Head to Head
| England League 1 | 2023/08/12 14:00 | Leyton Orient v Portsmouth | W | 0-4 |
| Club Friendly List | 2022/07/19 18:00 | Leyton Orient v Portsmouth | W | 2-5 |
| England League 2 | 2017/01/14 15:00 | Portsmouth v Leyton Orient | W | 2-1 |
| England League 2 | 2016/10/08 14:00 | Leyton Orient v Portsmouth | W | 0-1 |
| England League 2 | 2016/02/06 15:00 | Portsmouth v Leyton Orient | L | 0-1 |
| England League 2 | 2015/12/26 15:00 | Leyton Orient v Portsmouth | L | 3-2 |
Home History
| England League 1 | 2023/09/02 14:00 | Portsmouth v Peterborough | W | 3-1 |
| England EFL Cup | 2023/08/29 18:45 | Portsmouth v Peterborough | D | 1-1 |
| England League 1 | 2023/08/26 14:00 | Stevenage v Portsmouth | D | 0-0 |
| England EFL Trophy | 2023/08/22 18:45 | Portsmouth v Fulham U21 | D | 3-3 |
| England League 1 | 2023/08/19 14:00 | Portsmouth v Cheltenham | D | 0-0 |
| England League 1 | 2023/08/15 19:00 | Portsmouth v Exeter | W | 1-0 |
| England League 1 | 2023/08/12 14:00 | Leyton Orient v Portsmouth | W | 0-4 |
| England EFL Cup | 2023/08/08 18:45 | Forest Green v Portsmouth | W | 1-3 |
Away History
| England League 1 | 2023/09/02 14:00 | Leyton Orient v Stevenage | L | 0-3 |
| England League 1 | 2023/08/26 14:00 | Leyton Orient v Cambridge Utd | W | 2-0 |
| England League 1 | 2023/08/19 14:00 | Blackpool v Leyton Orient | D | 0-0 |
| England League 1 | 2023/08/15 18:45 | Wycombe v Leyton Orient | L | 3-2 |
| England League 1 | 2023/08/12 14:00 | Leyton Orient v Portsmouth | L | 0-4 |
| England EFL Cup | 2023/08/08 18:45 | Plymouth v Leyton Orient | L | 2-0 |
| England League 1 | 2023/08/05 14:00 | Charlton v Leyton Orient | L | 1-0 |
| Club Friendly List | 2023/08/01 18:45 | Bishop's Stortford v Leyton Orient | L | 1-0 |