| AFC Fylde v Chesterfield FC 16/02/2019 | View match | |
| Chesterfield FC v Harrogate Town 23/02/2019 | £9.50 | |
| Barnet FC v Chesterfield FC 26/02/2019 | View match | |
| Wrexham FC v Chesterfield FC 02/03/2019 | View match | |
| Braintree Town v Chesterfield FC 05/03/2019 | View match | |
| Chesterfield FC v Eastleigh 09/03/2019 | View match | |
| Bromley FC v Chesterfield FC 12/03/2019 | View match | |
| Havant & Waterlooville v Chesterfield FC 16/03/2019 | View match | |
| Chesterfield FC v Sutton United 23/03/2019 | View match | |
| Chesterfield FC v Dagenham & Redbridge 30/03/2019 | View match | |
| Dover Athletic FC v Chesterfield FC 06/04/2019 | View match | |
| Chesterfield FC v Maidstone United (1992) 13/04/2019 | View match |