| 1. Round | 10/04/1999 | Örgryte IS | - | Halmstads BK | 1:0 | ||||
| 2. Round | 17/04/1999 | IFK Norrköping | - | Örgryte IS | 0:2 |  |
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| 3. Round | 23/04/1999 | Örgryte IS | - | Malmö FF | 4:4 | ||||
| 4. Round | 02/05/1999 | Örebro SK | - | Örgryte IS | 0:1 | ||||
| 5. Round | 10/05/1999 | Örgryte IS | - | IFK Göteborg | 2:2 | |
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| 6. Round | 16/05/1999 | Djurgårdens IF | - | Örgryte IS | 0:3 | |
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| 10. Round | 12/06/1999 | Hammarby IF | - | Örgryte IS | 0:0 | ||||
| 11. Round | 19/06/1999 | Örgryte IS | - | Helsingborgs IF | 0:1 | ||||
| 12. Round | 26/06/1999 | Trelleborgs FF | - | Örgryte IS | 0:0 | ||||
| 15. Round | 01/08/1999 | Helsingborgs IF | - | Örgryte IS | 2:0 | ||||
| 16. Round | 08/08/1999 | Örgryte IS | - | Djurgårdens IF | 0:1 | ||||
| 17. Round | 14/08/1999 | IFK Göteborg | - | Örgryte IS | 1:0 | ||||
| 20. Round | 11/09/1999 | Kalmar FF | - | Örgryte IS | 2:2 | ||||
| 21. Round | 19/09/1999 | Örgryte IS | - | Örebro SK | 1:1 | ||||
| 22. Round | 26/09/1999 | Malmö FF | - | Örgryte IS | 1:1 | ||||
| 23. Round | 03/10/1999 | Västra Frölunda | - | Örgryte IS | 2:1 | ||||
| 24. Round | 15/10/1999 | Örgryte IS | - | AIK Solna | 1:1 | ||||
| 25. Round | 23/10/1999 | Örgryte IS | - | IFK Norrköping | 3:1 | |
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| 26. Round | 29/10/1999 | Halmstads BK | - | Örgryte IS | 0:0 |
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