| 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 |  |
|||
| League Two | 29/12/19 | Newport County | - | Leyton Orient | 1:1 | ||||
| League Two | 25/01/20 | Leyton Orient | - | Newport County | 2:1 | |
|||
| 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