| League Two | 07/12/19 | Oldham Athletic | - | Leyton Orient | 1:1 |  |
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| League Two | 21/01/20 | Leyton Orient | - | Northampton Town | 1:1 | ||||
| EFL Trophy | 08/12/20 | Leyton Orient | - | Bristol Rovers | 1:2 | ||||
| League Two | 09/03/21 | Leyton Orient | - | Stevenage FC | 0:0 | ||||
| League Two | 30/10/21 | Leyton Orient | - | Hartlepool United | 5:0 | ||||
| League One | 01/01/25 | Bristol Rovers | - | Leyton Orient | 2:3 | |
England