Jestrović started his playing career with Radnički Obrenovac in the early 1990s. 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 three years in France, representing SC Bastia (1997–1998) and Metz (1998–2000). He then moved to Belgian club Mouscron, having a lot of success in the 2000–01 season.
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 then spent a year and a half in the United Arab Emirates, playing for Al Ain and Al Nasr.
At international level, Jestrović represented Serbia and Montenegro from 2003 to 2005, making 12 appearances and scoring five goals.[1] His final international was an August 2005 friendly match away against Ukraine.[2]
