| 1. Round | 18/09/1999 | PS Kalamata | - | OFI Heraklion | 0:0 | ||||
| 5. Round | 23/10/1999 | PS Kalamata | - | Panachaiki GE | 1:1 | ||||
| 6. Round | 30/10/1999 | Ethnikos Asteras | - | PS Kalamata | 2:0 | ||||
| 7. Round | 06/11/1999 | PS Kalamata | - | AO Proodeftiki | 2:0 | ||||
| 8. Round | 20/11/1999 | Iraklis Saloniki | - | PS Kalamata | 2:1 | ||||
| 9. Round | 27/11/1999 | PS Kalamata | - | Panionios GSS | 1:3 |
Greece