| 7. Round | 06/11/1999 | PS Kalamata | - | AO Proodeftiki | 2:0 |  |
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| 9. Round | 27/11/1999 | PS Kalamata | - | Panionios GSS | 1:3 | |
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| 10. Round | 04/12/1999 | Paniliakos Pyrgos | - | PS Kalamata | 3:1 | |
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| 12. Round | 21/12/1999 | Olympiakos Piraeus | - | PS Kalamata | 4:1 | ||||
| 14. Round | 08/01/2000 | Ionikos Nikea | - | PS Kalamata | 0:1 |
Brazil