1. Round | 29/09/2019 | Apollon Pontou | - | PAE Chania | 0:4 | ||||
2. Round | 27/10/2019 | PAE Chania | - | Apollon Smyrnis | 0:1 | ||||
3. Round | 03/11/2019 | Platanias Chanion | - | PAE Chania | 1:1 | ||||
4. Round | 08/11/2019 | PAE Chania | - | PAS Giannina | 0:1 | ||||
6. Round | 24/11/2019 | AE Karaiskakis | - | PAE Chania | 0:0 | ||||
7. Round | 30/11/2019 | PAE Chania | - | Apollon Lárissa | 1:2 | ||||
8. Round | 09/12/2019 | Panachaiki GE | - | PAE Chania | 0:1 |