| Gillingham FC v Oldham Athletic FC 27/04/1966 | View match | |
| Gillingham FC v Walsall FC 30/04/1966 | View match | |
| Gillingham FC v Mansfield Town FC 03/05/1966 | View match | |
| Workington v Gillingham FC 07/05/1966 | View match | |
| Gillingham FC v Queens Park Rangers FC 18/05/1966 | £5.00 | |
| Gillingham FC v York City FC 21/05/1966 | View match | |
| Brentford FC v Gillingham FC 28/05/1966 | View match | |
| Scunthorpe United FC v Gillingham FC 20/08/1966 | View match | |
| Southend United FC v Gillingham FC 24/08/1966 | View match | |
| Gillingham FC v Workington 27/08/1966 | View match | |
| Gillingham FC v Southend United FC 31/08/1966 | View match | |
| Gillingham FC v Walsall FC 03/09/1966 | View match |