| League Two | 08/02/20 | Leyton Orient | - | Macclesfield Town | 1:1 | ||||
| League Two | 27/11/21 | Northampton Town | - | Leyton Orient | 1:0 | ||||
| League Two | 23/04/22 | Leyton Orient | - | Northampton Town | 2:4 | ||||
| League Two | 19/11/22 | Stockport County | - | Leyton Orient | 1:2 | ||||
| League Two | 29/04/23 | Leyton Orient | - | Stockport County | 0:3 | ||||
| League One | 21/09/24 | Stockport County | - | Leyton Orient | 1:4 | ||||
| Playoffs | 10/05/25 | Leyton Orient | - | Stockport County | 2:2 |  |
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| Playoffs | 14/05/25 | Stockport County | - | Leyton Orient | 1:4 pso |
England