| 1. Round | 09/04/1999 | Helsingborgs IF | - | IFK Göteborg | 3:1 |  |
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| 2. Round | 20/04/1999 | Hammarby IF | - | Helsingborgs IF | 2:1 | ||||
| 3. Round | 24/04/1999 | Helsingborgs IF | - | Djurgårdens IF | 4:1 | ||||
| 4. Round | 02/05/1999 | IFK Norrköping | - | Helsingborgs IF | 1:0 | ||||
| 6. Round | 16/05/1999 | Helsingborgs IF | - | Västra Frölunda | 1:0 | ||||
| 7. Round | 23/05/1999 | Helsingborgs IF | - | Örebro SK | 2:1 | ||||
| 8. Round | 29/05/1999 | Kalmar FF | - | Helsingborgs IF | 0:2 |  |
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| 9. Round | 09/06/1999 | Trelleborgs FF | - | Helsingborgs IF | 2:3 | |
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| 10. Round | 14/06/1999 | Helsingborgs IF | - | IF Elfsborg | 1:1 | ||||
| 11. Round | 19/06/1999 | Örgryte IS | - | Helsingborgs IF | 0:1 | ||||
| 12. Round | 22/06/1999 | Helsingborgs IF | - | Halmstads BK | 1:0 | |
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| 13. Round | 05/07/1999 | Malmö FF | - | Helsingborgs IF | 0:4 | |
Norway