| 1. Ronde | 20.09.1999 | Panathinaikos | - | AO Trikala | 2:0 |  |
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| 2. Ronde | 26.09.1999 | AEK Athene | - | Panathinaikos | 1:2 | |
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| 3. Ronde | 03.10.1999 | Panathinaikos | - | PAOK Saloniki | 1:1 | ||||
| 4. Ronde | 17.10.1999 | Panathinaikos | - | PS Kalamata | 5:0 | |
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| 5. Ronde | 25.10.1999 | Ethnikos Asteras | - | Panathinaikos | 1:2 | ||||
| 6. Ronde | 31.10.1999 | Panathinaikos | - | Iraklis Saloniki | 3:0 | |
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| 7. Ronde | 08.11.1999 | Paniliakos Pyrgos | - | Panathinaikos | 0:1 | ||||
| 8. Ronde | 21.11.1999 | Panathinaikos | - | Olympiakos | 2:0 | ||||
| 9. Ronde | 29.11.1999 | Ionikos Nikea | - | Panathinaikos | 2:2 | |
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| 10. Ronde | 05.12.1999 | Panathinaikos | - | Aris Saloniki | 3:0 | |
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