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| Wealdstone v Chesterfield FC 14/03/2023 | View match | |
| Woking FC v Chesterfield FC 18/03/2023 | View match | |
| Chesterfield FC v FC Halifax Town 25/03/2023 | View match | |
| Maidenhead United v Chesterfield FC 01/04/2023 | View match | |
| Chesterfield FC v York City FC 07/04/2023 | View match | |
| Dagenham & Redbridge v Chesterfield FC 10/04/2023 | View match | |
| Chesterfield FC v Eastleigh 15/04/2023 | View match | |
| Chesterfield FC v Torquay United FC 18/04/2023 | View match | |
| Bromley FC v Chesterfield FC 22/04/2023 | View match | |
| Chesterfield FC v Maidstone United (1992) 29/04/2023 | View match | |
| Notts County FC v Chesterfield FC 13/05/2023 | £8.00 |