Widely regarded as the greatest coach in European basketball history and outside the NBA,[1][2][3] Obradović has won a total of 64 club titles and honours over the course of his 30-year-long coaching career, including a record nine EuroLeague titles with five different clubs, along with 18 EuroLeague Final Four appearances.

In addition to his success at club level, he has also won major trophies as head coach of the Yugoslavia national team (present-day Serbia), most notably winning the gold medals at the 1997 EuroBasket and the 1998 FIBA World Championship.

In 2008, he was named one of the 50 Greatest EuroLeague Contributors, making the list as one of the ten head coaches that were chosen.

[5] Obradović started his club career as a basketball player with Borac Čačak, in their youth system.

He was brought in by Partizan's incoming head coach Moka Slavnić and vice president Dragan Kićanović, both recent retirees who had starred on the Yugoslav national team throughout the 1970s as a legendary guard duo.

Obradović's greatness as a professional club basketball coach, is fully confirmed by the great collection of titles he has acquired in his twenty-eight-year career as a head coach, including: a record 9 European-wide premiere level EuroLeague championships (won with five different teams), a record 14 EuroLeague Finals appearances, a record 18 EuroLeague Final Four appearances, two European-wide secondary level Saporta Cup championships, and numerous national domestic league championships and national cups.

Obradović's coaching career began quite suddenly in the summer of 1991 while he was still an active thirty-one-year-old Partizan player getting ready for EuroBasket 1991 with the Yugoslav national team.

Selected and coached by Dušan Ivković, the 1991 national squad was to be captained by Obradović—the oldest player among the assembled group.

However, after finishing the training camp in Poreč and coming back to Belgrade to sleep over before leaving in the morning for a preparation friendly tournament in Dortmund, Germany, Obradović got called in for a meeting with the Partizan management—club president Radojica Nikčević, vice-president Dragan Kićanović, as well as board members Đorđe "Siske" Čolović, Milorad "Miketa" Đurić, and Dragan Todorić—who convinced him to take over the Partizan head coaching job, which entailed retiring from playing effective immediately thus giving up a chance to captain the national team at the upcoming EuroBasket.

In his first season with the club, Real Madrid failed to defend the Liga ACB title, finishing in 3rd place with 27–19 record.

On the European scene, Obradović made his third consecutive Final Four appearance and second with Real Madrid, but ended losing in 3rd place game.

In 1996–97 season, Real Madrid finished as the runner-up in the Liga ACB and was also eliminated in the quarterfinals of the 1997 Copa del Rey de Baloncesto.

In European competitions, Real Madrid participated in second-tier FIBA Saporta Cup and eventually won it with 78–64 in the final game over Verona.

In the summer of 1997, in-demand Obradović, who had just won EuroBasket 1997 as FR Yugoslavia's head coach, made a high profile club move, signing with the Italian league champions Benetton Treviso thus succeeding Mike D'Antoni who had taken an offer from the NBA to join the Denver Nuggets' coaching staff as an assistant.

In his first season with the club, he won the 1999–2000 Greek Basket League with 3–0 record in the final series against PAOK Thessaloniki.

Following this disappointment, Panathinaikos lost to Olympiacos, 3 games to 2, in a best-of-five Greek League Finals series.

[10] After inheriting a roster with point guard Bo McCalebb and versatile shooting guards / small forwards Bojan Bogdanović and Emir Preldžić, the famous head coach added a pair of marquee forwards, in Linas Kleiza and Nemanja Bjelica.

He additionally signed Luka Žorić and Melih Mahmutoğlu, as well as talented youngsters Ömer Yurtseven and Kenan Sipahi.

In 2019–20 Basketbol Süper Ligi which was also cancelled in May for the same reason, Fenerbahçe was in fourth place with 17–5 record and one game behind the worse-record Galatasaray.

[19][20][21] In the 2021–22 EuroCup, Partizan was eliminated in eighfinals by Bursaspor at home court, which was considered a failure as one of the season goals was to run deep into the competition.

[23] Partizan ended the 2022–23 season by lifting the ABA League championship trophy, after 3–2 score against Crvena zvezda in the Finals series.

[27] He stands as the most successful head coach for the Serbia national team since the break-up of SFR Yugoslavia.

Well known for his temperamental approach, Obradović also has a reputation for being adaptable, with his ability to course correct on the fly underscored by a number of his coaching collaborators and rivals.

[28] He often utilized a system heavy on pick-and-rolls, focusing on using the corners and back passes to open up the offense and make it more difficult for the defense to commit.

In turn, Obradović, ahead of his second season coaching Fenerbahce, talked about spending a significant portion of the summer 2014 off-season, dissecting the San Antonio game, particularly positioning and ball movement, with a view of implementing it into his team.