| Leyton Orient FC v Crewe Alexandra FC 22/04/2023 | View match | |
| Mansfield Town FC v Leyton Orient FC 25/04/2023 | View match | |
| Leyton Orient FC v Stockport County FC 29/04/2023 | View match | |
| Bradford City FC v Leyton Orient FC 08/05/2023 | View match | |
| Charlton Athletic FC v Leyton Orient FC 05/08/2023 | £9.50 | |
| Plymouth Argyle FC v Leyton Orient FC 08/08/2023 | £7.00 | |
| Plymouth Argyle FC v Leyton Orient FC 08/08/2023 | £8.00 | |
| Leyton Orient FC v Portsmouth FC 12/08/2023 | View match | |
| Wycombe Wanderers FC v Leyton Orient FC 15/08/2023 | View match | |
| Blackpool FC v Leyton Orient FC 19/08/2023 | View match | |
| Leyton Orient FC v Cambridge United FC 26/08/2023 | View match | |
| Leyton Orient FC v Stevenage Borough FC 02/09/2023 | View match |