| 1. Round | 10/08/2019 | Arsenal FC [U18] | - | Chelsea FC [U18] | 1:2 | ||||
| 2. Round | 17/08/2019 | Chelsea FC [U18] | - | West Ham United [U18] | 4:3 | ||||
| 3. Round | 24/08/2019 | Southampton FC [U18] | - | Chelsea FC [U18] | 0:1 |  |
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| 4. Round | 31/08/2019 | Chelsea FC [U18] | - | Aston Villa [U18] | 1:0 | ||||
| 5. Round | 14/09/2019 | Brighton & Hove Albion [U18] | - | Chelsea FC [U18] | 1:1 | ||||
| 6. Round | 21/09/2019 | Chelsea FC [U18] | - | Reading FC [U18] | 2:1 | ||||
| 9. Round | 09/11/2019 | Tottenham Hotspur [U18] | - | Chelsea FC [U18] | 3:5 | |
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| 10. Round | 30/11/2019 | Chelsea FC [U18] | - | Fulham FC [U18] | 2:2 | ||||
| 11. Round | 07/12/2019 | Swansea City [U18] | - | Chelsea FC [U18] | 0:8 | |
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| 13. Round | 11/01/2020 | West Ham United [U18] | - | Chelsea FC [U18] | 2:1 | ||||
| 14. Round | 18/01/2020 | Aston Villa [U18] | - | Chelsea FC [U18] | 3:2 | |
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| 15. Round | 01/02/2020 | Chelsea FC [U18] | - | Southampton FC [U18] | 2:0 | |
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| 16. Round | 21/02/2020 | Chelsea FC [U18] | - | Brighton & Hove Albion [U18] | 4:0 |
England