Standing at 1.97 m (6 ft 5+1⁄2 in), he played in the guard position for Crvena zvezda, Limoges, Alba Berlin, Virtus Roma, Budućnost, and RheinEnergie Köln.

In 2018 Obradović won the Russian Cup with Lokomotiv Kuban, earning the EuroCup Coach of the Year award.

As a professional basketball player, Obradović played for Crvena zvezda, Limoges, Alba Berlin, Virtus Roma, Budućnost Podgorica and RheinEnergie Köln, until his retirement in 2005.

In April 2001, during his time with Budućnost, Obradović got into a fistfight with teammate Milenko Topić, during a practice session, and got suspended by the club.

Obradović had a key role in a 93–87 overtime win over Bulgaria when he scored the team-high 16 points and helped the team to qualify for Championship.

[2] Afterwards, he was a member of the national team led by head coach Dušan Ivković that won the gold medal at the 1995 Championship.

In the next year, Obradović was a member of the Yugoslavia team that won the gold medal at the FIBA World Championship in Greece.

[10] Obradović was a member of the Yugoslavia team led by head coach Svetislav Pešić that won the gold medal at the 2001 FIBA European Championship in Turkey.

[12] In November 2016, Obradović signed to be the head coach for the Russian club Lokomotiv Kuban of the VTB United League.

[16][17][18] Obradović got his first taste of the NBA through the Summer League coaching stints with the Brooklyn Nets, the Atlanta Hawks and the San Antonio Spurs.