| 2. Round | 02/10/2023 | PS Kalamata | - | AO Giouchtas | 3:1 | ||||
| 4. Round | 22/10/2023 | PS Kalamata | - | PAE Chania | 0:2 | ||||
| 5. Round | 28/10/2023 | PS Kalamata | - | GS Ilioupolis | 2:0 | ||||
| 6. Round | 05/11/2023 | Ionikos Nikea | - | PS Kalamata | 3:2 | ||||
| 7. Round | 11/11/2023 | PS Kalamata | - | AO Tilikratis | 3:0 | ||||
| 8. Round | 19/11/2023 | PS Kalamata | - | Diagoras FC | 1:2 |  |
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| 9. Round | 26/11/2023 | Olympiakos Piraeus II | - | PS Kalamata | 0:0 | ||||
| 10. Round | 03/12/2023 | PS Kalamata | - | Panachaiki GE | 1:0 | ||||
| 12. Round | 16/12/2023 | PS Kalamata | - | Panathinaikos II | 0:0 |
Portugal