| 1. Round | 17/09/1999 | AO Proodeftiki | - | Olympiakos Piraeus | 0:3 |  |
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| 9. Round | 28/11/1999 | Olympiakos Piraeus | - | Ethnikos Asteras | 5:0 |  |
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| 11. Round | 11/12/1999 | Olympiakos Piraeus | - | Paniliakos Pyrgos | 2:1 | ||||
| 12. Round | 21/12/1999 | Olympiakos Piraeus | - | PS Kalamata | 4:1 | |
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| 14. Round | 08/01/2000 | Olympiakos Piraeus | - | Aris Saloniki | 2:0 | ||||
| 15. Round | 15/01/2000 | OFI Heraklion | - | Olympiakos Piraeus | 2:1 | ||||
| 16. Round | 22/01/2000 | Olympiakos Piraeus | - | Skoda Xanthi | 3:2 | |
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| 17. Round | 28/01/2000 | Panachaiki GE | - | Olympiakos Piraeus | 0:2 | ||||
| 27. Round | 11/04/2000 | Olympiakos Piraeus | - | Iraklis Saloniki | 1:0 | |
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| 28. Round | 15/04/2000 | Paniliakos Pyrgos | - | Olympiakos Piraeus | 0:3 | |
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| 29. Round | 22/04/2000 | PS Kalamata | - | Olympiakos Piraeus | 0:1 | ||||
| 30. Round | 02/05/2000 | Olympiakos Piraeus | - | Ionikos Nikea | 2:0 | ||||
| 31. Round | 07/05/2000 | Aris Saloniki | - | Olympiakos Piraeus | 0:1 | |
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| 33. Round | 20/05/2000 | Skoda Xanthi | - | Olympiakos Piraeus | 0:1 | ||||
| 34. Round | 27/05/2000 | Olympiakos Piraeus | - | Panachaiki GE | 5:1 | |
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Brazil