| 1. Round | 09/11/2019 | Sunderland AFC | - | Gillingham FC | 1:1 | ||||
| 2. Round | 01/12/2019 | Gillingham FC | - | Doncaster Rovers | 3:0 | ||||
| 3. Round | 05/01/2020 | Gillingham FC | - | West Ham United | 0:2 |
| 1. Round | 09/11/2019 | Sunderland AFC | - | Gillingham FC | 1:1 | ||||
| 2. Round | 01/12/2019 | Gillingham FC | - | Doncaster Rovers | 3:0 | ||||
| 3. Round | 05/01/2020 | Gillingham FC | - | West Ham United | 0:2 |
| Thomas James O'Connor | |
| Born: | 21.04.1999 |
| Place of birth: |
Kilkenny, 
Ireland |
| Nationality: |
Ireland
|
| Position(s): | Left Back Defensive Midfielder |
| Foot: | left |
