The 1999–2000 Cypriot First Division was the 61st season of the Cypriot top-level football league. Anorthosis won their 11th title.
Format
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).
Point system
Teams received three points for a win, one point for a draw and zero points for a loss.
Changes from previous season
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.