[16] Leyton Orient 0-4 Portsmouth [13] 2023-08-12 14:00
Stadium: Matchroom Stadium Round: 2
Referee: Ollie Yates Home Manager: Richie Wellens Away Manager: John Mousinho
Head to Head
| Club Friendly List | 2022/07/19 18:00 | Leyton Orient v Portsmouth | L | 2-5 |
| England League 2 | 2017/01/14 15:00 | Portsmouth v Leyton Orient | L | 2-1 |
| England League 2 | 2016/10/08 14:00 | Leyton Orient v Portsmouth | L | 0-1 |
| England League 2 | 2016/02/06 15:00 | Portsmouth v Leyton Orient | W | 0-1 |
| England League 2 | 2015/12/26 15:00 | Leyton Orient v Portsmouth | W | 3-2 |
Home History
| 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 |
| Club Friendly List | 2023/07/29 14:00 | Colchester v Leyton Orient | L | 2-1 |
| Club Friendly List | 2023/07/25 18:45 | Dag & Red v Leyton Orient | D | 1-1 |
| Club Friendly List | 2023/07/19 18:45 | Ebbsfleet United v Leyton Orient | L | 3-2 |
| Club Friendly List | 2023/07/19 18:45 | Chelmsford v Leyton Orient | L | 2-0 |
| Club Friendly List | 2023/07/14 09:00 | Charlton v Leyton Orient | D | 1-1 |
Away History
| England EFL Cup | 2023/08/08 18:45 | Forest Green v Portsmouth | W | 1-3 |
| England League 1 | 2023/08/05 14:00 | Portsmouth v Bristol Rovers | D | 1-1 |
| Club Friendly List | 2023/07/29 14:00 | Portsmouth v Bristol City | L | 0-1 |
| Club Friendly List | 2023/07/25 18:00 | AFC Wimbledon v Portsmouth | L | 1-0 |
| Club Friendly List | 2023/07/15 12:00 | Havant and W v Portsmouth | W | 0-1 |
| Club Friendly List | 2023/07/14 18:00 | Gosport Borough v Portsmouth | W | 1-3 |
| Club Friendly List | 2023/07/11 18:45 | Bognor Regis Town v Portsmouth | D | 1-1 |
| Europe Friendlies | 2023/07/06 16:30 | Portsmouth v Europa FC | W | 1-0 |