| 2. Round | 28/08/2018 | AFC Bournemouth | - | Milton Keynes Dons | 3:0 | ||||
| 3. Round | 25/09/2018 | AFC Bournemouth | - | Blackburn Rovers | 3:2 | ||||
| Round of 16 | 30/10/2018 | AFC Bournemouth | - | Norwich City | 2:1 | ||||
| Quarter-finals | 19/12/2018 | Chelsea FC | - | AFC Bournemouth | 1:0 |  |
| 2. Round | 28/08/2018 | AFC Bournemouth | - | Milton Keynes Dons | 3:0 | ||||
| 3. Round | 25/09/2018 | AFC Bournemouth | - | Blackburn Rovers | 3:2 | ||||
| Round of 16 | 30/10/2018 | AFC Bournemouth | - | Norwich City | 2:1 | ||||
| Quarter-finals | 19/12/2018 | Chelsea FC | - | AFC Bournemouth | 1:0 | |
| Jack Benjamin Simpson | |
| Born: | 18.12.1996 |
| Place of birth: |
Weymouth, 
England |
| Nationality: |
England
|
| Height: | 190 cm |
| Weight: | 83 kg |
| Position(s): | Centre Back |
| Foot: | left |