| Gillingham FC v Reading FC 23/03/1966 | View match | |
| Brighton & Hove Albion FC v Gillingham FC 26/03/1966 | £5.00 | |
| Brighton & Hove Albion FC v Gillingham FC 26/03/1966 | £4.50 | |
| Shrewsbury Town FC v Gillingham FC 30/03/1966 | View match | |
| Gillingham FC v Bristol Rovers FC 02/04/1966 | View match | |
| Southend United FC v Gillingham FC 08/04/1966 | View match | |
| Walsall FC v Gillingham FC 09/04/1966 | View match | |
| Gillingham FC v Southend United FC 11/04/1966 | View match | |
| Gillingham FC v Oxford United FC 16/04/1966 | View match | |
| Swansea Town v Gillingham FC 23/04/1966 | View match | |
| Queens Park Rangers FC v Gillingham FC 25/04/1966 | View match | |
| Gillingham FC v Oldham Athletic FC 27/04/1966 | View match |