| Gillingham FC v Plymouth Argyle FC 09/05/2021 | View match | |
| Gillingham FC v Lincoln City FC 07/08/2021 | £7.50 | |
| Crawley Town FC v Gillingham FC 10/08/2021 | View match | |
| Plymouth Argyle FC v Gillingham FC 14/08/2021 | View match | |
| AFC Wimbledon FC v Gillingham FC 17/08/2021 | £7.50 | |
| Gillingham FC v Morecambe FC 21/08/2021 | £7.50 | |
| Gillingham FC v Cheltenham Town FC 24/08/2021 | View match | |
| Shrewsbury Town FC v Gillingham FC 28/08/2021 | View match | |
| Colchester United FC v Gillingham FC 07/09/2021 | View match | |
| Burton Albion FC v Gillingham FC 11/09/2021 | View match | |
| Gillingham FC v MK Dons (Milton Keynes Dons) 18/09/2021 | £7.50 | |
| Gillingham FC v Charlton Athletic FC 21/09/2021 | £7.50 |