| Competition: | Cypriot First Division |
| Season: | 1999–2000 |
| Winners: | Anorthosis (11th title) |
| Relegated: | Ethnikos Assia Anagennisi Alki |
| Continentalcup1: | Champions League |
| Continentalcup1 Qualifiers: | Anorthosis (2nd qualifying round) |
| Continentalcup2: | UEFA Cup |
| Continentalcup2 Qualifiers: | Omonia (qualifying round) APOEL (qualifying round; via Cypriot Cup) |
| Continentalcup3: | Intertoto Cup |
| Continentalcup3 Qualifiers: | Nea Salamis (1st round) |
| League Topscorer: | Rainer Rauffmann (34 goals)[1] |
| Matches: | 182 |
| Total Goals: | 670 |
| Prevseason: | 1998–99 |
| Nextseason: | 2000–01 |
The 1999–2000 Cypriot First Division was the 61st season of the Cypriot top-level football league. Anorthosis won their 11th title.
Fourteen teams participated in the 1999–2000 Cypriot First Division. All teams played against each other twice, once at their home and once away. The team with the most points at the end of the season crowned champions. The last three teams were relegated to the 2000–01 Cypriot Second Division.
The champions ensured their participation in the 2000–01 UEFA Champions League and the runners-up in the 2000–01 UEFA Cup.
The teams had to declare their interest to participate in the 2000 UEFA Intertoto Cup before the end of the championship. At the end of the championship, the higher placed team among the interested ones participated in the Intertoto Cup (if they had not secured their participation in any other UEFA competition).
Teams received three points for a win, one point for a draw and zero points for a loss.
Evagoras Paphos, Doxa Katokopia and Aris Limassol were relegated from previous season and played in the 1999–2000 Cypriot Second Division. They were replaced by the first three teams of the 1998–99 Cypriot Second Division, Anagennisi Deryneia, Ethnikos Assia and APOP Paphos.