| 11. Round | 10/12/1999 | PS Kalamata | - | Apollon Smyrnis | 1:1 | ||||
| 12. Round | 21/12/1999 | Olympiakos Piraeus | - | PS Kalamata | 4:1 | ||||
| 13. Round | 27/12/1999 | PS Kalamata | - | AO Kavala | 3:2 | ||||
| 17. Round | 30/01/2000 | PS Kalamata | - | AEK Athen | 1:1 | ||||
| 26. Round | 01/04/2000 | Panionios GSS | - | PS Kalamata | 2:0 | ||||
| 28. Round | 15/04/2000 | Apollon Smyrnis | - | PS Kalamata | 1:2 | ||||
| 29. Round | 22/04/2000 | PS Kalamata | - | Olympiakos Piraeus | 0:1 |
Greece