| 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 | ||||
| 22. Round | 04/03/2000 | Panathinaikos | - | Ethnikos Asteras | 4:0 | ||||
| 23. Round | 12/03/2000 | PS Kalamata | - | Ethnikos Asteras | 1:0 |
Kosovo