 |
 |
| Super League | 26/09/1999 | AO Trikala | - | Ethnikos Asteras | 1:2 | 2.600 |
| Super League | 16/10/1999 | AO Trikala | - | Paniliakos Pyrgos | 1:1 | 1.777 |
| Super League | 31/10/1999 | AO Trikala | - | Ionikos Nikea | 2:2 | 2.558 |
| Super League | 08/11/1999 | AO Trikala | - | Aris Saloniki | 0:1 | 1.527 |
| Super League | 28/11/1999 | AO Trikala | - | Skoda Xanthi | 2:1 | 2.388 |
| Super League | 05/12/1999 | Skoda Xanthi | - | AEK Athen | 2:2 | 2.767 |
| Super League | 12/12/1999 | AO Trikala | - | AO Proodeftiki | 0:0 | 1.575 |
| Friendlies | 18/12/1999 | Greece | - | Estonia | 2:2 | 6.145 |
| Super League | 29/12/1999 | AO Trikala | - | Apollon Smyrnis | 1:0 | 1.671 |
Greece