1. Round | 18/09/1999 | Kalamata | - | OFI Heraklion | 0:0 | ||||
2. Round | 25/09/1999 | PAOK Saloniki | - | Kalamata | 4:2 | ||||
3. Round | 02/10/1999 | Kalamata | - | Skoda Xanthi | 0:0 | ||||
4. Round | 16/10/1999 | Panathinaikos | - | Kalamata | 5:0 | ||||
5. Round | 23/10/1999 | Kalamata | - | Panachaiki GE | 1:1 | ||||
6. Round | 30/10/1999 | Ethnikos Asteras | - | Kalamata | 2:0 | ||||
7. Round | 06/11/1999 | Kalamata | - | AO Proodeftiki | 2:0 | ||||
8. Round | 20/11/1999 | Iraklis Saloniki | - | Kalamata | 2:1 | ||||
9. Round | 27/11/1999 | Kalamata | - | Panionios GSS | 1:3 | ||||
10. Round | 04/12/1999 | Paniliakos Pyrgos | - | Kalamata | 3:1 |