| 2. Round | 20/08/2018 | Blackburn Rovers U23 | - | Chelsea FC U23 | 0:3 | ||||
| 5. Round | 16/09/2018 | Chelsea FC U23 | - | Leicester City U23 | 1:1 | ||||
| 7. Round | 29/09/2018 | Chelsea FC U23 | - | Liverpool FC U23 | 1:3 |  |
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| 10. Round | 03/11/2018 | Arsenal FC U23 | - | Chelsea FC U23 | 4:5 | ||||
| 16. Round | 04/02/2019 | Derby County U23 | - | Chelsea FC U23 | 0:1 | ||||
| 17. Round | 15/02/2019 | Chelsea FC U23 | - | Swansea City U23 | 0:2 | ||||
| 18. Round | 01/03/2019 | Tottenham Hotspur U23 | - | Chelsea FC U23 | 1:1 | |
England
