He then played for OFK Beograd in the First League of FR Yugoslavia, before moving abroad for the first time in the summer of 1997.
Jestrović spent the best years of his career at Anderlecht (2001–2005), becoming the Belgian First Division top scorer in the 2004–05 season.
He made a total of 80 league appearances and scored 55 goals, before leaving the Brussels club in January 2006.
Jestrović also became the Serbian SuperLiga top scorer in the 2007–08 season while playing for Red Star Belgrade.
At international level, Jestrović represented Serbia and Montenegro from 2003 to 2005, making 12 appearances and scoring five goals.