1. Round | 03/08/2019 | Doncaster Rovers | - | Gillingham FC | 1:1 | ||||
2. Round | 10/08/2019 | Gillingham FC | - | Burton Albion | 1:2 | ||||
4. Round | 20/08/2019 | Gillingham FC | - | Blackpool FC | 2:2 | ||||
5. Round | 24/08/2019 | Coventry City | - | Gillingham FC | 1:0 | ||||
10. Round | 21/09/2019 | Gillingham FC | - | Ipswich Town | 0:1 | ||||
13. Round | 12/10/2019 | Portsmouth FC | - | Gillingham FC | 0:0 | ||||
15. Round | 22/10/2019 | Shrewsbury Town | - | Gillingham FC | 1:1 |