| 1er tour | 19.06.1999 | Cementarnica Skopje | - | Kolkheti-1913 Poti | 4:2 |  |
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| 1er tour | 26.06.1999 | Kolkheti-1913 Poti | - | Cementarnica Skopje | 0:4 | ||||
| 2e tour | 03.07.1999 | Cementarnica Skopje | - | Rostselmash Rostov | 1:1 | ||||
| 2e tour | 10.07.1999 | Rostselmash Rostov | - | Cementarnica Skopje | 2:1 |
Macédoine du Nord