| Gillingham FC v Millwall FC 23/08/1958 | View match | |
| Carlisle United FC v Gillingham FC 26/08/1958 | View match | |
| Walsall FC v Gillingham FC 30/08/1958 | View match | |
| Gillingham FC v Carlisle United FC 01/09/1958 | View match | |
| Gillingham FC v Darlington FC 06/09/1958 | View match | |
| Gillingham FC v Barrow 10/09/1958 | View match | |
| Shrewsbury Town FC v Gillingham FC 13/09/1958 | View match | |
| Barrow v Gillingham FC 15/09/1958 | View match | |
| Gillingham FC v Coventry City FC 20/09/1958 | View match | |
| Oldham Athletic FC v Gillingham FC 22/09/1958 | View match | |
| Exeter City FC v Gillingham FC 27/09/1958 | View match | |
| Gillingham FC v Oldham Athletic FC 01/10/1958 | View match |