| 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 |  |
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| 3. Ronde | 25.09.2020 | Brighton & Hove Albion U23 | - | Chelsea FC U23 | 2:0 | ||||
| 4. Ronde | 04.10.2020 | Chelsea FC U23 | - | Arsenal FC U23 | 3:0 | |
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| 5. Ronde | 17.10.2020 | Chelsea FC U23 | - | Derby County U23 | 3:2 | |
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| 8. Ronde | 08.11.2020 | Everton FC U23 | - | Chelsea FC U23 | 2:0 | ||||
| 9. Ronde | 22.11.2020 | Manchester City U23 | - | Chelsea FC U23 | 2:2 | |
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| 7. Ronde | 04.12.2020 | Chelsea FC U23 | - | Leicester City U23 | 2:1 | |
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| 11. Ronde | 14.12.2020 | Chelsea FC U23 | - | Tottenham Hotspur U23 | 3:2 | |
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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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