1. Round | 03/08/2019 | Doncaster Rovers | - | Gillingham FC | 1:1 | ||||
2. Round | 10/08/2019 | Gillingham FC | - | Burton Albion | 1:2 | ||||
5. Round | 24/08/2019 | Coventry City | - | Gillingham FC | 1:0 | ||||
7. Round | 07/09/2019 | Tranmere Rovers | - | Gillingham FC | 2:2 | ||||
8. Round | 14/09/2019 | Gillingham FC | - | Wycombe Wanderers | 2:0 | ||||
9. Round | 17/09/2019 | Bristol Rovers | - | Gillingham FC | 1:1 | ||||
12. Round | 05/10/2019 | Gillingham FC | - | Southend United | 3:1 | ||||
13. Round | 12/10/2019 | Portsmouth FC | - | Gillingham FC | 0:0 | ||||
14. Round | 19/10/2019 | Gillingham FC | - | Peterborough United | 1:2 | ||||
15. Round | 22/10/2019 | Shrewsbury Town | - | Gillingham FC | 1:1 | ||||
16. Round | 26/10/2019 | Accrington Stanley | - | Gillingham FC | 0:1 | ||||
17. Round | 02/11/2019 | Gillingham FC | - | Rotherham United | 0:3 |