1. Round | 18/09/1999 | Panionios GSS | - | Paniliakos Pyrgos | 1:2 | ||||
2. Round | 24/09/1999 | Apollon Smyrnis | - | Paniliakos Pyrgos | 0:0 | ||||
4. Round | 15/10/1999 | AO Trikala | - | Paniliakos Pyrgos | 1:1 | ||||
6. Round | 30/10/1999 | PAOK Saloniki | - | Paniliakos Pyrgos | 0:1 | ||||
7. Round | 07/11/1999 | Paniliakos Pyrgos | - | Panathinaikos | 0:1 | ||||
8. Round | 20/11/1999 | Ethnikos Asteras | - | Paniliakos Pyrgos | 3:1 | ||||
10. Round | 04/12/1999 | Paniliakos Pyrgos | - | Kalamata | 3:1 | ||||
11. Round | 11/12/1999 | Olympiakos Piraeus | - | Paniliakos Pyrgos | 2:1 | ||||
12. Round | 21/12/1999 | Paniliakos Pyrgos | - | Ionikos Nikea | 3:0 |