| 1. Ronde | 11.08.2023 | Chelsea FC U21 | - | Blackburn Rovers U21 | 6:1 |  |
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| 2. Ronde | 18.08.2023 | Chelsea FC U21 | - | Brighton & Hove Albion U21 | 2:3 | ||||
| 3. Ronde | 25.08.2023 | Norwich City U21 | - | Chelsea FC U21 | 3:2 | ||||
| 11. Ronde | 12.01.2024 | Chelsea FC U21 | - | Manchester United U21 | 3:2 |  |
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| 13. Ronde | 09.02.2024 | West Ham United U21 | - | Chelsea FC U21 | 0:2 | ||||
| 14. Ronde | 19.02.2024 | Leeds United U21 | - | Chelsea FC U21 | 0:2 | ||||
| 9. Ronde | 23.02.2024 | Middlesbrough FC U21 | - | Chelsea FC U21 | 1:3 | ||||
| 15. Ronde | 01.03.2024 | Chelsea FC U21 | - | Arsenal FC U21 | 2:4 | |
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| 18. Ronde | 08.04.2024 | Aston Villa U21 | - | Chelsea FC U21 | 0:4 | ||||
| 19. Ronde | 12.04.2024 | Crystal Palace U21 | - | Chelsea FC U21 | 2:2 | |
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| 20. Ronde | 26.04.2024 | Chelsea FC U21 | - | Southampton FC U21 | 2:0 |
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