| 13. Round | 05/07/1999 | Malmö FF | - | Helsingborgs IF | 0:4 | ||||
| 14. Round | 10/07/1999 | Halmstads BK | - | Helsingborgs IF | 4:0 | ||||
| 15. Round | 01/08/1999 | Helsingborgs IF | - | Örgryte IS | 2:0 | ||||
| 16. Round | 06/08/1999 | Västra Frölunda | - | Helsingborgs IF | 0:0 | ||||
| 17. Round | 14/08/1999 | Helsingborgs IF | - | AIK Solna | 0:2 | ||||
| 19. Round | 29/08/1999 | IF Elfsborg | - | Helsingborgs IF | 1:1 | ||||
| 20. Round | 10/09/1999 | Helsingborgs IF | - | Trelleborgs FF | 5:3 | ||||
| 21. Round | 19/09/1999 | Helsingborgs IF | - | IFK Norrköping | 0:1 | ||||
| 22. Round | 24/09/1999 | Djurgårdens IF | - | Helsingborgs IF | 2:4 |  |
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| 23. Round | 03/10/1999 | Helsingborgs IF | - | Kalmar FF | 3:0 | ||||
| 24. Round | 11/10/1999 | Örebro SK | - | Helsingborgs IF | 0:1 | ||||
| 25. Round | 23/10/1999 | Helsingborgs IF | - | Hammarby IF | 2:0 | ||||
| 26. Round | 29/10/1999 | IFK Göteborg | - | Helsingborgs IF | 0:1 |
Norway