| EFL Trophy | 02/09/14 | Peterborough United | - | Leyton Orient | 2:3 | ||||
| League One | 13/12/14 | Leyton Orient | - | Peterborough United | 1:2 | ||||
| League Two | 06/02/16 | Portsmouth FC | - | Leyton Orient | 0:1 | ||||
| League Two | 08/10/16 | Leyton Orient | - | Portsmouth FC | 0:1 |  |
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| League Two | 14/01/17 | Portsmouth FC | - | Leyton Orient | 2:1 |
England