Head to Head
| 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
| UK Friendlies | 2022/07/12 18:45 | Maidstone Utd v Leyton Orient | D | 0-0 |
| Club Friendly List | 2022/07/08 10:00 | Leyton Orient v Peterborough | L | 0-3 |
| Club Friendly List | 2022/07/04 17:30 | Leyton Orient v West Brom | L | 1-2 |
| Club Friendly List | 2022/07/01 18:00 | Haringey Borough v Leyton Orient | W | 1-2 |
| England League 2 | 2022/05/07 14:00 | Leyton Orient v Tranmere | L | 0-1 |
| England League 2 | 2022/04/30 14:00 | Crawley Town v Leyton Orient | W | 0-2 |
| England League 2 | 2022/04/23 14:00 | Leyton Orient v Northampton | L | 2-4 |
| England League 2 | 2022/04/18 14:00 | Swindon v Leyton Orient | W | 1-2 |
Away History
| Club Friendly List | 2022/07/16 12:00 | Gillingham v Portsmouth | W | 1-2 |
| Europe Friendlies | 2022/07/09 14:00 | Portsmouth v Qatar SC Doha | W | 2-0 |
| Europe Friendlies | 2022/07/03 14:00 | Gosport Borough v Portsmouth | L | 1-0 |
| Club Friendly List | 2022/07/02 14:00 | Havant and W v Portsmouth | W | 0-3 |
| England League 1 | 2022/04/30 11:30 | Sheff Wed v Portsmouth | L | 4-1 |
| England League 1 | 2022/04/26 18:45 | Portsmouth v Wigan | W | 3-2 |
| England League 1 | 2022/04/23 14:00 | Portsmouth v Gillingham | W | 3-1 |
| England League 1 | 2022/04/18 14:00 | Morecambe v Portsmouth | D | 1-1 |