| League Cup | 09/08/11 | Southend United | - | Leyton Orient | 3:4 pso | ||||
| League One | 06/04/15 | Leyton Orient | - | Gillingham FC | 3:3 | ||||
| League Two | 26/12/16 | Leyton Orient | - | Crawley Town | 3:2 | ||||
| League Two | 25/03/17 | Crawley Town | - | Leyton Orient | 3:0 | ||||
| League Two | 24/08/19 | Leyton Orient | - | Crawley Town | 2:3 | ||||
| League Two | 19/12/20 | Leyton Orient | - | Crawley Town | 1:2 | ||||
| League Two | 02/02/21 | Crawley Town | - | Leyton Orient | 0:0 | ||||
| League Two | 11/12/21 | Leyton Orient | - | Crawley Town | 1:2 | ||||
| League Two | 30/04/22 | Crawley Town | - | Leyton Orient | 0:2 | ||||
| League Two | 25/10/22 | Leyton Orient | - | Gillingham FC | 2:0 | ||||
| League Two | 18/04/23 | Gillingham FC | - | Leyton Orient | 2:0 | ||||
| EFL Trophy | 05/09/23 | Gillingham FC | - | Leyton Orient | 2:1 |
England