| 1. Round | 24/09/2023 | Kozani FC | - | Aiolikos Mytilinis | 1:2 |  |
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| 2. Round | 02/10/2023 | Aiolikos Mytilinis | - | Makedonikos FC | 1:3 | ||||
| 3. Round | 11/10/2023 | Anagennisi Karditsa | - | Aiolikos Mytilinis | 3:1 | ||||
| 5. Round | 21/10/2023 | PAOK Saloniki II | - | Aiolikos Mytilinis | 0:0 | ||||
| 8. Round | 12/11/2023 | Levadiakos | - | Aiolikos Mytilinis | 2:0 | ||||
| 9. Round | 15/11/2023 | Aiolikos Mytilinis | - | Niki Volou FC | 0:2 |
Greece