| 2. Round | 24/09/1999 | Apollon Smyrnis | - | Paniliakos Pyrgos | 0:0 | ||||
| 3. Round | 02/10/1999 | Apollon Smyrnis | - | Olympiakos Piraeus | 0:1 |  |
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| 4. Round | 16/10/1999 | Ionikos Nikea | - | Apollon Smyrnis | 1:0 | ||||
| 6. Round | 31/10/1999 | OFI Heraklion | - | Apollon Smyrnis | 1:0 | |
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| 8. Round | 20/11/1999 | Panachaiki GE | - | Apollon Smyrnis | 1:2 | |
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| 9. Round | 27/11/1999 | Apollon Smyrnis | - | AO Proodeftiki | 0:2 | ||||
| 11. Round | 10/12/1999 | PS Kalamata | - | Apollon Smyrnis | 1:1 | |
Greece