| 2. Round | 24/09/2000 | Skoda Xanthi | - | PS Kalamata | 2:1 | ||||
| 5. Round | 04/11/2000 | PS Kalamata | - | Ethnikos Asteras | 2:2 | ||||
| 6. Round | 11/11/2000 | Ionikos Nikea | - | PS Kalamata | 4:1 | ||||
| 7. Round | 18/11/2000 | PS Kalamata | - | AEK Athen | 3:1 |  |
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| 8. Round | 25/11/2000 | Panachaiki GE | - | PS Kalamata | 3:2 | ||||
| 9. Round | 02/12/2000 | Olympiakos Piraeus | - | PS Kalamata | 5:2 | ||||
| 10. Round | 09/12/2000 | PS Kalamata | - | PAS Giannina | 3:4 | ||||
| 14. Round | 13/01/2001 | PS Kalamata | - | Paniliakos Pyrgos | 1:1 | |
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| 23. Round | 17/03/2001 | PS Kalamata | - | Panachaiki GE | 3:3 |
Greece