| 2. Round | 25/09/1999 | AO Trikala | - | Ethnikos Asteras | 1:2 | ||||
| 8. Round | 20/11/1999 | Ethnikos Asteras | - | Paniliakos Pyrgos | 3:1 | ||||
| 9. Round | 28/11/1999 | Olympiakos Piraeus | - | Ethnikos Asteras | 5:0 |  |
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| 11. Round | 11/12/1999 | Aris Saloniki | - | Ethnikos Asteras | 1:1 | ||||
| 12. Round | 21/12/1999 | Ethnikos Asteras | - | OFI Heraklion | 0:1 | ||||
| 13. Round | 28/12/1999 | Skoda Xanthi | - | Ethnikos Asteras | 0:0 | ||||
| 14. Round | 08/01/2000 | Panachaiki GE | - | Ethnikos Asteras | 2:0 | ||||
| 22. Round | 04/03/2000 | Panathinaikos | - | Ethnikos Asteras | 4:0 | |
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| 24. Round | 19/03/2000 | Ethnikos Asteras | - | Iraklis Saloniki | 3:1 | ||||
| 25. Round | 25/03/2000 | Paniliakos Pyrgos | - | Ethnikos Asteras | 2:0 | ||||
| 33. Round | 20/05/2000 | Ethnikos Asteras | - | Panionios GSS | 4:2 |
Greece