Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 19.09.1999 |  | Matchday 1 | Kalamata - OFI | - OFI | 0:0 | 2.649 |
| 03.10.1999 | | Matchday 3 | Kalamata - Xhanti FC | - Xan | 0:0 | 2.988 |
| 24.10.1999 | | Matchday 5 | Kalamata - Panachaiki GE | - Pan | 1:1 | 2.452 |
| 07.11.1999 | | Matchday 7 | Kalamata - AO Proodeftiki | - | 2:0 | 1.051 |
| 28.11.1999 | | Matchday 9 | Kalamata - Panionios | - Pan | 1:3 | 1.911 |
| 11.12.1999 | | Matchday 11 | Kalamata - Apollon | - Smy | 1:1 | 520 |
| 28.12.1999 | | Matchday 13 | Kalamata - AO Kavala | - AO | 3:2 | 1.053 |