| Gillingham FC v Colchester United FC 19/10/1957 | View match | |
| Norwich City FC v Gillingham FC 26/10/1957 | View match | |
| Walsall FC v Gillingham FC 09/11/1957 | £35.00 | |
| Gillingham FC v Gorleston 16/11/1957 | View match | |
| Shrewsbury Town FC v Gillingham FC 23/11/1957 | View match | |
| Gillingham FC v Reading FC 30/11/1957 | View match | |
| Millwall FC v Gillingham FC 07/12/1957 | View match | |
| Gillingham FC v Millwall FC 11/12/1957 | View match | |
| Gillingham FC v Watford FC 14/12/1957 | View match | |
| Brighton & Hove Albion FC v Gillingham FC 21/12/1957 | View match | |
| Gillingham FC v Queens Park Rangers FC 25/12/1957 | View match | |
| Queens Park Rangers FC v Gillingham FC 26/12/1957 | View match |