| 1. Round | 10/08/2019 | B.93 København [Youth] | - | Hellerup IK [Youth] | 2:1 | ||||
| 2. Round | 17/08/2019 | AC Horsens [Youth] | - | Hellerup IK [Youth] | 4:2 |  |
 |
||
| 3. Round | 24/08/2019 | Hobro IK [Youth] | - | Hellerup IK [Youth] | 2:2 | ||||
| 4. Round | 31/08/2019 | Hellerup IK [Youth] | - | Kolding IF [Youth] | 0:2 | ||||
| 5. Round | 07/09/2019 | Hellerup IK [Youth] | - | Viborg FF [Youth] | 2:5 | |
|||
| 6. Round | 14/09/2019 | FC Helsingør [Youth] | - | Hellerup IK [Youth] | 7:0 | ||||
| 7. Round | 21/09/2019 | Hellerup IK [Youth] | - | FC Roskilde [Youth] | 3:4 | ||||
| 9. Round | 05/10/2019 | Hellerup IK [Youth] | - | Slagelse B&I [Youth] | 2:2 | ||||
| 10. Round | 12/10/2019 | Næstved BK [Youth] | - | Hellerup IK [Youth] | 2:2 | ||||
| 12. Round | 26/10/2019 | Næsby BK [Youth] | - | Hellerup IK [Youth] | 3:0 | ||||
| 14. Round | 09/11/2019 | Holbæk B&I [Youth] | - | Hellerup IK [Youth] | 0:3 | |
|||
| 16. Round | 23/11/2019 | Hellerup IK [Youth] | - | B.93 København [Youth] | 2:2 | ||||
| 11. Round | 07/03/2020 | Hellerup IK [Youth] | - | HB Køge [Youth] | 3:1 |
Denmark