| 1. Ronde | 14.09.2020 | Chelsea FC U23 | - | West Ham United U23 | 1:0 | ||||
| 2. Ronde | 18.09.2020 | Southampton FC U23 | - | Chelsea FC U23 | 1:4 | ||||
| 17. Ronde | 05.02.2021 | Arsenal FC U23 | - | Chelsea FC U23 | 2:2 | ||||
| 18. Ronde | 15.02.2021 | Derby County U23 | - | Chelsea FC U23 | 2:1 |  |
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| 19. Ronde | 19.02.2021 | Chelsea FC U23 | - | Liverpool FC U23 | 2:3 | ||||
| 20. Ronde | 01.03.2021 | Leicester City U23 | - | Chelsea FC U23 | 1:1 | |
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| 16. Ronde | 07.03.2021 | Chelsea FC U23 | - | Brighton & Hove Albion U23 | 0:0 | ||||
| 21. Ronde | 12.03.2021 | Chelsea FC U23 | - | Everton FC U23 | 2:1 | ||||
| 22. Ronde | 21.03.2021 | Chelsea FC U23 | - | Manchester City U23 | 2:2 | ||||
| 14. Ronde | 06.04.2021 | West Ham United U23 | - | Chelsea FC U23 | 1:1 | |
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| 15. Ronde | 12.04.2021 | Chelsea FC U23 | - | Southampton FC U23 | 3:1 |  |
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| 24. Ronde | 18.04.2021 | Tottenham Hotspur U23 | - | Chelsea FC U23 | 1:4 | |
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| 25. Ronde | 23.04.2021 | Manchester United U23 | - | Chelsea FC U23 | 4:2 | |
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| 26. Ronde | 30.04.2021 | Chelsea FC U23 | - | Blackburn Rovers U23 | 1:0 | ||||
| 13. Ronde | 07.05.2021 | Blackburn Rovers U23 | - | Chelsea FC U23 | 2:4 |
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