| 1. Round | 10/08/2019 | B.93 København [Youth B] | - | Hellerup IK [Youth B] | 6:4 |  |
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| 2. Round | 17/08/2019 | AC Horsens [Youth B] | - | Hellerup IK [Youth B] | 3:2 | |
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| 3. Round | 24/08/2019 | Hobro IK [Youth B] | - | Hellerup IK [Youth B] | 2:5 | ||||
| 4. Round | 31/08/2019 | Hellerup IK [Youth B] | - | Kolding IF [Youth B] | 1:1 | ||||
| 6. Round | 14/09/2019 | FC Helsingør [Youth B] | - | Hellerup IK [Youth B] | 1:0 | ||||
| 7. Round | 21/09/2019 | Hellerup IK [Youth B] | - | FC Roskilde [Youth B] | 2:1 | ||||
| 9. Round | 05/10/2019 | Hellerup IK [Youth B] | - | Slagelse B&I [Youth B] | 5:2 | ||||
| 10. Round | 12/10/2019 | Næstved BK [Youth B] | - | Hellerup IK [Youth B] | 0:0 |  |
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| 14. Round | 09/11/2019 | Holbæk B&I [Youth B] | - | Hellerup IK [Youth B] | 2:3 | ||||
| 16. Round | 23/11/2019 | Hellerup IK [Youth B] | - | B.93 København [Youth B] | 0:1 | |
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| 11. Round | 07/03/2020 | Hellerup IK [Youth B] | - | HB Køge [Youth B] | 2:2 | |
Denmark