| Port Vale FC v Gillingham FC 21/03/1959 | View match | |
| Gillingham FC v Aldershot F.C 27/03/1959 | View match | |
| Gillingham FC v Crystal Palace FC 28/03/1959 | View match | |
| Aldershot F.C v Gillingham FC 30/03/1959 | View match | |
| Chester City FC v Gillingham FC 04/04/1959 | View match | |
| Gillingham FC v Torquay United FC 08/04/1959 | View match | |
| Gillingham FC v Watford FC 11/04/1959 | View match | |
| Darlington FC v Gillingham FC 16/04/1959 | View match | |
| Hartlepool United v Gillingham FC 18/04/1959 | View match | |
| Gateshead v Gillingham FC 20/04/1959 | View match | |
| Gillingham FC v Southport 25/04/1959 | View match | |
| Torquay United FC v Gillingham FC 29/04/1959 | View match |