| Date | Match | Score | Competition |
|---|---|---|---|
| 1999-12-28 | KalamataKavalaSuper League · Greece | 3–2 | Super League · Greece |
| 1999-12-22 | OlympiakosKalamataSuper League · Greece | 4–1 | Super League · Greece |
| 1999-12-11 | KalamataApollonSuper League · Greece | 1–1 | Super League · Greece |
| 1999-12-05 | PaniliakosKalamataSuper League · Greece | 3–1 | Super League · Greece |
| 1999-11-28 | KalamataPanioniosSuper League · Greece | 1–3 | Super League · Greece |
| 1999-11-21 | IraklisKalamataSuper League · Greece | 2–1 | Super League · Greece |
| 1999-11-07 | KalamataProodeytikiSuper League · Greece | 2–0 | Super League · Greece |
| 1999-10-31 | Ethnikos AsterasKalamataSuper League · Greece | 2–0 | Super League · Greece |
| 1999-10-24 | KalamataPanahaikiSuper League · Greece | 1–1 | Super League · Greece |
| 1999-10-17 | PanathinaikosKalamataSuper League · Greece | 5–0 | Super League · Greece |
| 1999-10-03 | KalamataXanthiSuper League · Greece | 0–0 | Super League · Greece |
| 1999-09-26 | PAOKKalamataSuper League · Greece | 4–2 | Super League · Greece |
| 1999-09-19 | KalamataOFISuper League · Greece | 0–0 | Super League · Greece |