| Gillingham FC v Southport 26/09/1959 | View match | |
| Gillingham FC v Workington 30/09/1959 | View match | |
| Millwall FC v Gillingham FC 03/10/1959 | View match | |
| Gillingham FC v Torquay United FC 07/10/1959 | View match | |
| Bradford Park Avenue v Gillingham FC 10/10/1959 | View match | |
| Gillingham FC v Stockport County FC 17/10/1959 | View match | |
| Exeter City FC v Gillingham FC 24/10/1959 | View match | |
| Gillingham FC v Watford FC 31/10/1959 | View match | |
| Oldham Athletic FC v Gillingham FC 07/11/1959 | View match | |
| Bedford Town v Gillingham FC 14/11/1959 | View match | |
| Notts County FC v Gillingham FC 21/11/1959 | View match | |
| Gillingham FC v Walsall FC 28/11/1959 | View match |