| League One | 30/03/19 | Gillingham FC | - | Rochdale AFC | 1:1 | ||||
| FA Cup | 19/11/19 | Gillingham FC | - | Sunderland AFC | 1:0 aet | ||||
| League One | 01/01/20 | Gillingham FC | - | Portsmouth FC | 1:1 | ||||
| League One | 08/02/20 | Burton Albion | - | Gillingham FC | 0:0 | ||||
| FA Cup | 28/11/20 | Gillingham FC | - | Exeter City | 2:3 | ||||
| League One | 26/01/21 | Gillingham FC | - | Crewe Alexandra | 4:1 | ||||
| League One | 09/05/21 | Gillingham FC | - | Plymouth Argyle | 1:0 | ||||
| League One | 26/02/22 | Portsmouth FC | - | Fleetwood Town | 3:3 | ||||
| League One | 13/08/22 | Cheltenham Town | - | Portsmouth FC | 0:2 |
England