| 1. Round | 14/09/2020 | Chelsea FC U23 | - | West Ham United U23 | 1:0 | ||||
| 2. Round | 18/09/2020 | Southampton FC U23 | - | Chelsea FC U23 | 1:4 |  |
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| 3. Round | 25/09/2020 | Brighton & Hove Albion U23 | - | Chelsea FC U23 | 2:0 | ||||
| 4. Round | 04/10/2020 | Chelsea FC U23 | - | Arsenal FC U23 | 3:0 | |
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| 5. Round | 17/10/2020 | Chelsea FC U23 | - | Derby County U23 | 3:2 | |
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| 8. Round | 08/11/2020 | Everton FC U23 | - | Chelsea FC U23 | 2:0 | ||||
| 9. Round | 22/11/2020 | Manchester City U23 | - | Chelsea FC U23 | 2:2 | |
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| 7. Round | 04/12/2020 | Chelsea FC U23 | - | Leicester City U23 | 2:1 | |
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| 11. Round | 14/12/2020 | Chelsea FC U23 | - | Tottenham Hotspur U23 | 3:2 | |
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| 25. Round | 23/04/2021 | Manchester United U23 | - | Chelsea FC U23 | 4:2 | |
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| 26. Round | 30/04/2021 | Chelsea FC U23 | - | Blackburn Rovers U23 | 1:0 | ||||
| 13. Round | 07/05/2021 | Blackburn Rovers U23 | - | Chelsea FC U23 | 2:4 |
England