| 1. Jornada | 20.08.2023 | OFI Heraklion | - | Aris Saloniki | 3:2 |  |
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| 2. Jornada | 26.08.2023 | Asteras Tripolis | - | OFI Heraklion | 3:0 | ||||
| 3. Jornada | 03.09.2023 | OFI Heraklion | - | PAOK Saloniki | 1:0 | ||||
| 4. Jornada | 16.09.2023 | Lamia | - | OFI Heraklion | 2:2 | ||||
| 5. Jornada | 23.09.2023 | OFI Heraklion | - | Atromitos | 1:1 | ||||
| 6. Jornada | 27.09.2023 | Panetolikos | - | OFI Heraklion | 1:1 | ||||
| 7. Jornada | 02.10.2023 | OFI Heraklion | - | AEK Athen | 2:0 | ||||
| 8. Jornada | 22.10.2023 | AE Kifisias | - | OFI Heraklion | 0:0 | |
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| 9. Jornada | 30.10.2023 | OFI Heraklion | - | Olympiacos | 0:2 | ||||
| 10. Jornada | 06.11.2023 | Panserraikos | - | OFI Heraklion | 2:1 | |
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| 12. Jornada | 24.11.2023 | OFI Heraklion | - | Volos NFC | 1:1 | ||||
| 13. Jornada | 03.12.2023 | Panathinaikos | - | OFI Heraklion | 4:0 | |
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| 15. Jornada | 21.12.2023 | OFI Heraklion | - | Asteras Tripolis | 0:2 |
Chipre