| 1. Round | 18/09/1999 | Ethnikos Asteras | - | AO Kavala | 1:0 | ||||
| 2. Round | 25/09/1999 | AO Trikala | - | Ethnikos Asteras | 1:2 |  |
|||
| 3. Round | 02/10/1999 | Ethnikos Asteras | - | AEK Athen | 1:3 | ||||
| 5. Round | 24/10/1999 | Ethnikos Asteras | - | Panathinaikos | 1:2 | ||||
| 6. Round | 30/10/1999 | Ethnikos Asteras | - | PS Kalamata | 2:0 | ||||
| 7. Round | 06/11/1999 | Iraklis Saloniki | - | Ethnikos Asteras | 2:0 | ||||
| 8. Round | 20/11/1999 | Ethnikos Asteras | - | Paniliakos Pyrgos | 3:1 | |
|||
| 9. Round | 28/11/1999 | Olympiakos Piraeus | - | Ethnikos Asteras | 5:0 | ||||
| 10. Round | 05/12/1999 | Ethnikos Asteras | - | Ionikos Nikea | 1:2 | ||||
| 11. Round | 11/12/1999 | Aris Saloniki | - | Ethnikos Asteras | 1:1 |  |
|||
| 12. Round | 21/12/1999 | Ethnikos Asteras | - | OFI Heraklion | 0:1 | |
|||
| 14. Round | 08/01/2000 | Panachaiki GE | - | Ethnikos Asteras | 2:0 | ||||
| 16. Round | 22/01/2000 | Panionios GSS | - | Ethnikos Asteras | 1:0 | ||||
| 18. Round | 05/02/2000 | AO Kavala | - | Ethnikos Asteras | 2:0 | ||||
| 19. Round | 12/02/2000 | Ethnikos Asteras | - | AO Trikala | 1:0 |
Greece