| Competition: | Macedonian First League |
| Season: | 1999–2000 |
| Winners: | Sloga Jugomagnat 2nd domestic title |
| Relegated: | Napredok Kumanovo |
| Continentalcup1: | Champions League |
| Continentalcup1 Qualifiers: | Sloga Jugomagnat |
| Continentalcup2: | UEFA Cup |
| Continentalcup2 Qualifiers: | Pobeda Rabotnichki |
| Continentalcup3: | Intertoto Cup |
| Continentalcup3 Qualifiers: | Pelister |
| League Topscorer: | Argjend Beqiri (19 goals) |
| Dates: | 15 August 1999 – 28 May 2000 |
| Biggest Home Win: | Napredok 10–0 Kumanovo |
| Biggest Away Win: | Kumanovo 0–8 Vardar Napredok 0–8 Pobeda |
| Highest Scoring: | Napredok 10–0 Kumanovo |
| Matches: | 182 |
| Total Goals: | 524 |
| Prevseason: | 1998–99 |
| Nextseason: | 2000–01 |
The 1999–2000 Macedonian First League was the 8th season of the Macedonian First Football League, the highest football league of Macedonia. The first matches of the season were played on 15 August 1999 and the last on 28 May 2000. Sloga Jugomagnat defended their championship title, having won their second title in a row.
Relegated to 2000–01 Second League
|
Relegated to 2000–01 Second League |
| Rank | Player | Club | Goals |
|---|---|---|---|
| 1 | Argjend Beqiri | Sloga Jugomagnat | 19 |
| 2 | Dejan Ristovski | Cementarnica | 16 |
| 3 | Dejvi Glavevski | Pelister | 13 |
| Nikolche Zdravevski | Pobeda | ||
| 5 | Antonio Tasev | Tikvesh | 12 |
| 6 | Toni Micevski | Pelister | 11 |
| 7 | Zhanko Savov | Cementarnica | 10 |
| Goran Petreski | Vardar | ||
| Zoran Miserdovski | Sloga Jugomagnat | ||
| Dragan Dimitrovski | Tikvesh | ||
Source: Top15goalscorers.blogspot.com