| Gillingham FC v Charlton Athletic FC 09/05/1959 | View match | |
| Gillingham FC v Gateshead 22/08/1959 | View match | |
| Rochdale FC v Gillingham FC 27/08/1959 | View match | |
| Darlington FC v Gillingham FC 29/08/1959 | View match | |
| Gillingham FC v Rochdale FC 03/09/1959 | View match | |
| Gillingham FC v Aldershot F.C 05/09/1959 | View match | |
| Northampton Town FC v Gillingham FC 10/09/1959 | View match | |
| Barrow v Gillingham FC 12/09/1959 | View match | |
| Gillingham FC v Northampton Town FC 16/09/1959 | £7.00 | |
| Gillingham FC v Chester City FC 19/09/1959 | View match | |
| Workington v Gillingham FC 24/09/1959 | View match | |
| Gillingham FC v Southport 26/09/1959 | View match |