| 1. Round | 19/09/1999 | PAOK Saloniki | - | AEK Athen | 4:4 | ||||
| 2. Round | 25/09/1999 | PAOK Saloniki | - | PS Kalamata | 4:2 |  |
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| 3. Round | 02/10/1999 | Panathinaikos | - | PAOK Saloniki | 1:1 | ||||
| 5. Round | 23/10/1999 | Iraklis Saloniki | - | PAOK Saloniki | 3:1 | ||||
| 6. Round | 30/10/1999 | PAOK Saloniki | - | Paniliakos Pyrgos | 0:1 | ||||
| 7. Round | 07/11/1999 | Olympiakos Piraeus | - | PAOK Saloniki | 4:1 | ||||
| 8. Round | 20/11/1999 | PAOK Saloniki | - | Ionikos Nikea | 3:0 | |
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| 9. Round | 27/11/1999 | Aris Saloniki | - | PAOK Saloniki | 0:0 | ||||
| 10. Round | 04/12/1999 | OFI Heraklion | - | PAOK Saloniki | 2:0 |  |
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| 11. Round | 11/12/1999 | PAOK Saloniki | - | Skoda Xanthi | 5:0 | |
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| 12. Round | 20/12/1999 | Panachaiki GE | - | PAOK Saloniki | 1:2 | ||||
| 13. Round | 28/12/1999 | PAOK Saloniki | - | AO Proodeftiki | 1:0 |
Egypt