| 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 | |
| AFC Fylde v Chesterfield FC 12/08/2023 | View match | |
| Oxford City FC v Chesterfield FC 15/08/2023 | View match | |
| Chesterfield FC v Oldham Athletic FC 19/08/2023 | View match | |
| Altrincham v Chesterfield FC 26/08/2023 | View match |