| 1. Round | 12/08/2019 | Derby County U23 | - | Chelsea FC U23 | 0:1 | ||||
| 2. Round | 19/08/2019 | Chelsea FC U23 | - | Liverpool FC U23 | 3:0 | ||||
| 3. Round | 23/08/2019 | Manchester City U23 | - | Chelsea FC U23 | 2:2 |
| 1. Round | 12/08/2019 | Derby County U23 | - | Chelsea FC U23 | 0:1 | ||||
| 2. Round | 19/08/2019 | Chelsea FC U23 | - | Liverpool FC U23 | 3:0 | ||||
| 3. Round | 23/08/2019 | Manchester City U23 | - | Chelsea FC U23 | 2:2 |
| Juan Carlos Familia-Castillo | |
| Born: | 13.01.2000 |
| Place of birth: |
Amsterdam, 
Netherlands |
| Nationality: |
Dom. Republic
Netherlands |
| Height: | 177 cm |
| Weight: | 77 kg |
| Position(s): | Left Back Left Midfielder |
| Foot: | left |