| 1. Round | 09/08/2019 | Holbæk B&I [Youth B] | - | FC Roskilde [Youth B] | 0:0 | ||||
| 3. Round | 24/08/2019 | B.93 København [Youth B] | - | FC Roskilde [Youth B] | 6:3 | ||||
| 4. Round | 31/08/2019 | FC Roskilde [Youth B] | - | AC Horsens [Youth B] | 2:5 | ||||
| 6. Round | 14/09/2019 | FC Roskilde [Youth B] | - | Kolding IF [Youth B] | 0:0 | ||||
| 7. Round | 21/09/2019 | Hellerup IK [Youth B] | - | FC Roskilde [Youth B] | 2:1 | ||||
| 8. Round | 28/09/2019 | FC Roskilde [Youth B] | - | FC Helsingør [Youth B] | 5:2 | ||||
| 9. Round | 05/10/2019 | FC Roskilde [Youth B] | - | Viborg FF [Youth B] | 3:0 | ||||
| 14. Round | 09/11/2019 | Næsby BK [Youth B] | - | FC Roskilde [Youth B] | 1:1 | ||||
| 15. Round | 16/11/2019 | FC Roskilde [Youth B] | - | AB Gladsaxe [Youth B] | 0:3 | ||||
| 16. Round | 24/11/2019 | FC Roskilde [Youth B] | - | Holbæk B&I [Youth B] | 3:1 |  |
Denmark