| League Two | 02.01.16 | Stevenage FC | - | Leyton Orient | 2:2 | ||||
| League Two | 19.04.16 | Leyton Orient | - | Plymouth Argyle | 1:3 | ||||
| League Two | 19.11.16 | Leyton Orient | - | Blackpool FC | 1:2 |  |
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| League Two | 29.12.19 | Newport County | - | Leyton Orient | 1:1 | ||||
| League Two | 25.01.20 | Leyton Orient | - | Newport County | 2:1 | |
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| League Cup | 05.09.20 | Forest Green Rovers | - | Leyton Orient | 1:2 | ||||
| League Two | 03.11.20 | Forest Green Rovers | - | Leyton Orient | 2:1 | ||||
| League Two | 23.01.21 | Leyton Orient | - | Forest Green Rovers | 0:1 | ||||
| League Two | 19.10.21 | Leyton Orient | - | Forest Green Rovers | 1:1 | ||||
| League Two | 15.03.22 | Forest Green Rovers | - | Leyton Orient | 1:1 | ||||
| League Two | 11.02.23 | Walsall FC | - | Leyton Orient | 1:1 |
Jamaica