| 14. Round | 04/02/2023 | FC Helsingør [Youth] | - | Næsby BK [Youth] | 4:1 pso |  |
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| 16. Round | 04/03/2023 | AC Amager Academy [Youth] | - | FC Helsingør [Youth] | 7:6 pso | ||||
| 17. Round | 11/03/2023 | FC Helsingør [Youth] | - | Kolding IF [Youth] | 2:5 | |
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| 18. Round | 18/03/2023 | SfB-Oure FA [Youth] | - | FC Helsingør [Youth] | 3:5 pso |  |
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| 19. Round | 25/03/2023 | FC Helsingør [Youth] | - | Nykøbing FC [Youth] | 3:1 | ||||
| 20. Round | 01/04/2023 | HB Køge [Youth] | - | FC Helsingør [Youth] | 3:2 | ||||
| 29. Round | 06/04/2023 | Næsby BK [Youth] | - | FC Helsingør [Youth] | 1:2 | |
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| 21. Round | 16/04/2023 | FC Helsingør [Youth] | - | AB Gladsaxe [Youth] | 3:5 | ||||
| 22. Round | 22/04/2023 | FC Roskilde [Youth] | - | FC Helsingør [Youth] | 5:0 | ||||
| 23. Round | 29/04/2023 | FC Helsingør [Youth] | - | Hvidovre IF [Youth] | 5:0 | |
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| 24. Round | 06/05/2023 | Næstved BK [Youth] | - | FC Helsingør [Youth] | 1:0 | |
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| 25. Round | 13/05/2023 | FC Helsingør [Youth] | - | B.93 København [Youth] | 2:4 pso | |
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| 27. Round | 27/05/2023 | FC Helsingør [Youth] | - | Hobro IK [Youth] | 0:3 | ||||
| 30. Round | 18/06/2023 | IF Lyseng [Youth] | - | FC Helsingør [Youth] | 6:5 pso |
Denmark