| 1. Round | 14/08/2016 | Sunderland AFC U23 | - | Chelsea FC U23 | 1:1 | ||||
| 2. Round | 22/08/2016 | Chelsea FC U23 | - | Liverpool FC U23 | 4:1 | ||||
| 3. Round | 28/08/2016 | Manchester United U23 | - | Chelsea FC U23 | 1:1 | ||||
| 7. Round | 14/10/2016 | Chelsea FC U23 | - | Leicester City U23 | 0:0 | ||||
| 9. Round | 31/10/2016 | Everton FC U23 | - | Chelsea FC U23 | 1:1 | ||||
| 12. Round | 09/12/2016 | Chelsea FC U23 | - | Manchester United U23 | 3:1 | ||||
| 15. Round | 13/01/2017 | Leicester City U23 | - | Chelsea FC U23 | 0:4 | ||||
| 17. Round | 05/02/2017 | Chelsea FC U23 | - | Reading FC U23 | 2:0 | ||||
| 18. Round | 18/02/2017 | Chelsea FC U23 | - | Manchester City U23 | 3:4 | ||||
| 20. Round | 13/03/2017 | Liverpool FC U23 | - | Chelsea FC U23 | 2:0 | ||||
| 13. Round | 05/05/2017 | Derby County U23 | - | Chelsea FC U23 | 2:1 |
Gambia