| 1. Ronde | 10.08.2019 | Arsenal FC [U18] | - | Chelsea FC [U18] | 1:2 |  |
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| 2. Ronde | 17.08.2019 | Chelsea FC [U18] | - | West Ham United [U18] | 4:3 | |
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| 3. Ronde | 24.08.2019 | Southampton FC [U18] | - | Chelsea FC [U18] | 0:1 | ||||
| 4. Ronde | 31.08.2019 | Chelsea FC [U18] | - | Aston Villa [U18] | 1:0 | |
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| 5. Ronde | 14.09.2019 | Brighton & Hove Albion [U18] | - | Chelsea FC [U18] | 1:1 | |
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| 6. Ronde | 21.09.2019 | Chelsea FC [U18] | - | Reading FC [U18] | 2:1 | ||||
| 7. Ronde | 05.10.2019 | Leicester City [U18] | - | Chelsea FC [U18] | 1:4 | |
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| 9. Ronde | 09.11.2019 | Tottenham Hotspur [U18] | - | Chelsea FC [U18] | 3:5 | |
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| 10. Ronde | 30.11.2019 | Chelsea FC [U18] | - | Fulham FC [U18] | 2:2 | |
Engeland