| Competition: | Belgian First Division |
| Season: | 1999–2000 |
| Winners: | Anderlecht |
| Relegated: | Geel Lommel |
| Continentalcup1: | Champions League |
| Continentalcup1 Qualifiers: | Anderlecht |
| Continentalcup2: | UEFA Cup |
| Continentalcup2 Qualifiers: | Club Brugge Gent |
| League Topscorer: | Ole Martin Årst Toni Brogno (30 each) |
| Matches: | 306 |
| Total Goals: | 1032 |
| Prevseason: | 1998–99 |
| Nextseason: | 2000–01 |
The 1999–2000 season of the Jupiler League was held between August 6, 1999, and May 11, 2000. Sporting Anderlecht became champions.
These teams were promoted from the second division at the start of the season:
These teams were relegated to the second division at the end of the season:
Anderlecht became champions on April 21, 2000, after the defeat of rival Club Brugge at Herman Vanderpoortenstadion to Lierse 1-0 as, prior to these results, they were 7 points ahead of Brugge with 3 matches to go. The next day Anderlecht beat Racing Genk 4-1 and then Standard Liège 2-0.
Club Brugge and Gent qualified for the UEFA Cup.
Charleroi avoided relegation with a controversial draw against Anderlecht on the last day of the season. Anderlecht were already champions and played with Enzo Scifo who had previously signed a deal with Charleroi. However, the result was irrelevant as Geel lost their last match to Club Brugge and were thus relegated with Lommel.
| Scorer | Goals | Team | |
|---|---|---|---|
 Ole Martin Årst | 30 | Gent | |
 Toni Brogno | 30 | Westerlo | |
 Jan Koller | 20 | Anderlecht | |
| David Paas | 19 | Harelbeke | |
| Eric Van Meir | 15 | Lierse | |
 Tomasz Radzinski | 14 | Anderlecht | |
| Dante Brogno | 14 | Charleroi | |
 Marcin Żewłakow | 14 | Mouscron | |
 Pär Zetterberg | 14 | Anderlecht |