2. Round | 25/09/1999 | OFI Heraklion | - | Skoda Xanthi | 2:1 | ||||
3. Round | 02/10/1999 | Kalamata | - | Skoda Xanthi | 0:0 | ||||
4. Round | 16/10/1999 | Skoda Xanthi | - | Panachaiki GE | 1:0 | ||||
5. Round | 23/10/1999 | AO Proodeftiki | - | Skoda Xanthi | 0:0 | ||||
6. Round | 30/10/1999 | Skoda Xanthi | - | Panionios GSS | 5:0 | ||||
7. Round | 06/11/1999 | Apollon Smyrnis | - | Skoda Xanthi | 0:0 | ||||
8. Round | 19/11/1999 | Skoda Xanthi | - | AO Kavala | 1:0 | ||||
9. Round | 27/11/1999 | AO Trikala | - | Skoda Xanthi | 2:1 | ||||
10. Round | 04/12/1999 | Skoda Xanthi | - | AEK Athen | 2:2 | ||||
11. Round | 11/12/1999 | PAOK Saloniki | - | Skoda Xanthi | 5:0 | ||||
12. Round | 22/12/1999 | Skoda Xanthi | - | Panathinaikos | 1:3 | ||||
14. Round | 08/01/2000 | Iraklis Saloniki | - | Skoda Xanthi | 3:1 | ||||
15. Round | 14/01/2000 | Skoda Xanthi | - | Paniliakos Pyrgos | 1:0 | ||||
16. Round | 22/01/2000 | Olympiakos Piraeus | - | Skoda Xanthi | 3:2 | ||||
17. Round | 29/01/2000 | Skoda Xanthi | - | Ionikos Nikea | 2:1 |