| 1. Round | 11/04/1999 | IF Elfsborg | - | Kalmar FF | 3:0 | ||||
| 2. Round | 17/04/1999 | Kalmar FF | - | Trelleborgs FF | 3:2 | ||||
| 13. Round | 03/07/1999 | Kalmar FF | - | IFK Göteborg | 0:1 | ||||
| 14. Round | 13/07/1999 | Kalmar FF | - | Hammarby IF | 4:1 | ||||
| 15. Round | 31/07/1999 | IFK Norrköping | - | Kalmar FF | 4:2 | ||||
| 16. Round | 07/08/1999 | Örebro SK | - | Kalmar FF | 2:0 |  |
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| 17. Round | 14/08/1999 | Kalmar FF | - | Malmö FF | 1:0 | ||||
| 18. Round | 21/08/1999 | IFK Göteborg | - | Kalmar FF | 2:0 | ||||
| 19. Round | 28/08/1999 | Halmstads BK | - | Kalmar FF | 1:0 | ||||
| 20. Round | 11/09/1999 | Kalmar FF | - | Örgryte IS | 2:2 | |
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| 21. Round | 18/09/1999 | Västra Frölunda | - | Kalmar FF | 2:0 | |
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| 23. Round | 03/10/1999 | Helsingborgs IF | - | Kalmar FF | 3:0 | ||||
| 25. Round | 23/10/1999 | Trelleborgs FF | - | Kalmar FF | 1:0 |
Sweden