| 1. Round | 18/09/1999 | Iraklis Saloniki | - | Apollon Smyrnis | 1:0 | ||||
| 2. Round | 26/09/1999 | AO Kavala | - | Iraklis Saloniki | 3:1 | ||||
| 5. Round | 23/10/1999 | Iraklis Saloniki | - | PAOK Saloniki | 3:1 |  |
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| 7. Round | 06/11/1999 | Iraklis Saloniki | - | Ethnikos Asteras | 2:0 | ||||
| 9. Round | 27/11/1999 | Paniliakos Pyrgos | - | Iraklis Saloniki | 4:3 |  |
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| 10. Round | 03/12/1999 | Iraklis Saloniki | - | Olympiakos Piraeus | 3:4 |
Bosnia-Herzegovina