| 3. Round | 02/10/1999 | Iraklis Saloniki | - | AO Trikala | 4:1 |  |
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| 4. Round | 16/10/1999 | AEK Athen | - | Iraklis Saloniki | 3:2 | |
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| 11. Round | 11/12/1999 | Ionikos Nikea | - | Iraklis Saloniki | 1:1 | ||||
| 21. Round | 26/02/2000 | Iraklis Saloniki | - | AEK Athen | 3:1 | ||||
| 26. Round | 01/04/2000 | Iraklis Saloniki | - | Paniliakos Pyrgos | 3:1 | ||||
| 28. Round | 15/04/2000 | Iraklis Saloniki | - | Ionikos Nikea | 3:2 | |
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| 32. Round | 13/05/2000 | Iraklis Saloniki | - | Panachaiki GE | 2:1 | |
Greece
Romania