After Dragan Okuka retired he would move back to Yugoslavia and returned to his first club Velež Mostar, where he took the position of General Manager within the team by 1990. His time at the club was short-lived, and he would soon have to face challenges outside football when his life would be disrupted by the Bosnian War in 1992, however in 1994 Dragan would make his first foray into management when he was hired by struggling Yugoslavian team FK Bečej and lead them to fourth within the 1994–95 league season. This would be enough for Dragan to lead the team to the 1995 UEFA Intertoto Cup, where the club were knocked out in the group stages; however, despite this, Dragan would soon attract the interests of FK Čukarički Stankom, who he stayed with for one season.
Still regarded as one of the country's most promising coaches, he would join highly ambitious football club FK Obilić despite the questionable ownership of career criminal Željko Ražnatović. While at the club he would employ a 3-5-2 formation as the club won the 1997–98 league title for the first time. Dragan would only stay with the club for one season, as Željko Ražnatović's ownership of the club came into question, and, despite having the chance to manage in the 1998–99 UEFA Champions League, Dragan decided to join FK Budućnost Podgorica the following season.
After a short stint with FK Vojvodina, Dragan would move away from the Yugoslavian league and join top tier Polish side Legia Warsaw, where he would soon get them to play in a 3-4-1-2 formation and eventually aid them to the 2001–02 Ekstraklasa league title at the end of the season. The following season wasn't so happy for Dragan, as Legia Warsaw were knocked out early within the 2002–03 UEFA Champions League while also having an underwhelming league season, which saw him replaced by Dariusz Kubicki at the end of the season.
After spending eighteen months out of coaching, he was offered the chance to manage the Serbia and Montenegro U-21 team, where he used a 4-4-2 formation to help guide the team to the 2006 European Under-21 Championship. At the tournament he would go on to guide the club to a semi-final position as the team narrowly missed the final in a penalty shoot-out against Ukraine. Once the tournament finished Dragan would return to club football with Polish side Wisła Kraków, who were looking for someone to improve upon their last season's result of second within the league. Already several games into the season expectations were still high despite the previous manager Dan Petrescu being fired after a slow start; however, Dragan was not the manager to change the club's fortunes and was fired two months later after only eight games, with the club languishing in mid-table.
Dragan would move around Europe, first with Cypriot side AC Omonia, where he played a 4-2-3-1 formation with little success before leaving the club after only several months. He wouldn't wait too long before joining Bulgarian side Lokomotiv Sofia in June 2008; however, the highlight of his reign was a short stint within the 2008–09 UEFA Cup, and, after being unable to mount a title challenge during his time with the club, they decided not to renew his contract. This saw him move to Greek side Kavala F.C., but he only stayed with the club for five mouths and was replaced with Henryk Kasperczak. Deciding not to stay within Europe, Dragan would accept the management position from Chinese top-tier football club Jiangsu Sainty, who he joined half-way through their 2011 league season and within his debut season guided the club to their best-ever finish of fourth at the end of the campaign. He would strive to made Jiangsu Sainty the Chinese Super League runner-up in 2012, with only 4points to equal Marcello Lippi's Guangzhou Evergrande at the end of the season. Okuka would receive the honour of Chinese Football Association : Coach of the Year for his wonderful coaching performance in 2012 and he was to gain popularity among soccer fans throughout China. Okuka won his first title for Jiangsu in the 2013 Chinese FA Super Cup bu beating Super League and FA Cup winners Guangzhou Evergrande 2-1. However, Jiangsu Sainty spent most time in struggling at the edge of relegation in the 2013 season and finally avoided relegation by beating Qingdao Jonoon just one point. The club decided not to extended his contract at the end of the season.