| League Two | 21/12/19 | Cambridge United | - | Leyton Orient | 2:3 | ||||
| League Two | 07/03/20 | Leyton Orient | - | Cambridge United | 2:1 | ||||
| League Two | 26/12/20 | Cambridge United | - | Leyton Orient | 2:1 | ||||
| League Two | 20/04/21 | Leyton Orient | - | Cambridge United | 2:4 | ||||
| League Two | 08/10/22 | Doncaster Rovers | - | Leyton Orient | 1:1 | ||||
| League Two | 07/01/23 | Leyton Orient | - | Doncaster Rovers | 1:0 | ||||
| League Two | 29/04/23 | Leyton Orient | - | Stockport County | 0:3 |
England