Obradović made his senior debut with Radnički Beograd in the mid-1990s, before moving to Obilić in the 1998–99 season. While playing for the Knights, Obradović established himself as one of the best defenders in the league. In the summer of 2001, Obradović was transferred to Russian club Lokomotiv Moscow.
Obradović played seven seasons for Ukrainian club Metalist Kharkiv from 2006 to 2013, spending the last six months of his contract on loan at Arsenal Kyiv.
On 23 July 2013, Obradović signed a one-year contract with Partizan.[2] On 27 July 2014, Obradović signed with OFK Beograd.[3]
Obradović retired in January 2015 and immediately became the assistant manager of Slavko Matić at FK Napredak Kruševac.[4] It lasted until 25 May 2015, where the duo was fired.
Obradović continued alongside Slavko Matić and became his assistant at Slovenian club FC Koper in October 2015.[5] On 22 March 2016, he then became the manager of Slovenian club FC Koper.[6] The club decided to change manage on 26 September 2016 which meant, that Obradović left the club.[7]
On 18 February 2017, Obradović was presented as the new manager of the Serbian U19 national team.[8] In May 2017, Obradović found an agreement with FK Spartak Subotica and the club announced him as the new manager from the new season. Only few days later it came out, that Obradović had called the management of the club to tell them, that he had accepted a more lucrative offer from another club.[9] However, the deal was only a verbal agreement and never became official.