| 1. Round | 12/08/2018 | Chelsea FC U23 | - | Everton FC U23 | 1:1 | ||||
| 2. Round | 20/08/2018 | Blackburn Rovers U23 | - | Chelsea FC U23 | 0:3 |  |
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| 3. Round | 24/08/2018 | Chelsea FC U23 | - | Derby County U23 | 0:1 | ||||
| 12. Round | 07/12/2018 | Chelsea FC U23 | - | West Ham United U23 | 3:2 | |
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| 13. Round | 17/12/2018 | Leicester City U23 | - | Chelsea FC U23 | 2:1 | ||||
| 18. Round | 01/03/2019 | Tottenham Hotspur U23 | - | Chelsea FC U23 | 1:1 | ||||
| 19. Round | 08/03/2019 | Chelsea FC U23 | - | Manchester City U23 | 2:0 | |
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| 20. Round | 06/04/2019 | Liverpool FC U23 | - | Chelsea FC U23 | 3:2 |  |
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| 21. Round | 15/04/2019 | Chelsea FC U23 | - | Arsenal FC U23 | 1:3 | ||||
| 22. Round | 03/05/2019 | Brighton & Hove Albion U23 | - | Chelsea FC U23 | 1:2 |
England
Scotland