| Torquay United FC v Gillingham FC 09/12/1959 | View match | |
| Gillingham FC v Crewe Alexandra FC 12/12/1959 | View match | |
| Gateshead v Gillingham FC 19/12/1959 | View match | |
| Crystal Palace FC v Gillingham FC 28/12/1959 | View match | |
| Gillingham FC v Darlington FC 02/01/1960 | View match | |
| Gillingham FC v Swansea Town 09/01/1960 | View match | |
| Aldershot F.C v Gillingham FC 16/01/1960 | View match | |
| Gillingham FC v Barrow 23/01/1960 | View match | |
| Hartlepool United v Gillingham FC 30/01/1960 | View match | |
| Chester City FC v Gillingham FC 06/02/1960 | View match | |
| Southport v Gillingham FC 13/02/1960 | View match | |
| Gillingham FC v Millwall FC 20/02/1960 | View match |