| 1. Runde | 13.08.2019 | Colchester United | - | Swindon Town | 3:0 |  |
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| 2. Runde | 27.08.2019 | Crystal Palace | - | Colchester United | 4:5 i.E. | ||||
| 3. Runde | 24.09.2019 | Colchester United | - | Tottenham Hotspur | 4:3 i.E. | ||||
| Achtelfinale | 29.10.2019 | Crawley Town | - | Colchester United | 1:3 | ||||
| Viertelfinale | 18.12.2019 | Manchester United | - | Colchester United | 3:0 |
England