| Chesterfield FC v Bury FC 27/03/1959 | View match | |
| Chesterfield FC v Tranmere Rovers FC 28/03/1959 | View match | |
| Bury FC v Chesterfield FC 30/03/1959 | £10.00 | |
| Stockport County FC v Chesterfield FC 04/04/1959 | View match | |
| Chesterfield FC v Bournemouth & Boscombe 11/04/1959 | View match | |
| Chesterfield FC v Stockport County FC 13/04/1959 | View match | |
| Colchester United FC v Chesterfield FC 18/04/1959 | View match | |
| Chesterfield FC v Reading FC 25/04/1959 | £7.99 | |
| Norwich City FC v Chesterfield FC 29/04/1959 | View match | |
| Grimsby Town FC v Chesterfield FC 22/08/1959 | View match | |
| Chesterfield FC v Southampton FC 24/08/1959 | View match | |
| Chesterfield FC v Queens Park Rangers FC 29/08/1959 | View match |