| 20. Round | 10/09/1999 | Helsingborgs IF | - | Trelleborgs FF | 5:3 | ||||
| 23. Round | 02/10/1999 | Trelleborgs FF | - | Örebro SK | 2:1 |  |
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| 24. Round | 17/10/1999 | Malmö FF | - | Trelleborgs FF | 1:2 | |
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| 25. Round | 23/10/1999 | Trelleborgs FF | - | Kalmar FF | 1:0 | ||||
| 26. Round | 29/10/1999 | Hammarby IF | - | Trelleborgs FF | 4:0 | |
Sweden