Career
College soccer
Jakovic took up association football in Canada. He was a four-year letterwinner at Scarlett Heights Academy, and was named team Most Valuable Player as a junior and senior, captaining both indoor and outdoor teams. At the age of 18 Jakovic had a trial with OFK Beograd, but was not signed by the team
Instead, Jakovic accepted a scholarship to the University of Alabama at Birmingham, and went on to play four years of college soccer for the Blazers.
Red Star Belgrade
On 28 June 2008, Jakovic joined Red Star Belgrade in preparations for the upcoming 2008-2009 season, after successfully completing a tryout with the team He officially signed with the club on 30 June 2008.
Jakovic made three league starts at the beginning of the season under head coach Zdeněk Zeman. However, following the coaching change on 6 September 2008, Dejan lost his spot in the team, and failed to register a single league appearance following the appointment of new head coach Čedomir Janevski.
After the completion of the 2008 half-season Red Star began looking at options to move him.
In December it was reported that he would be sent to FK Rad along with Marko Blažić, another player who started under Zeman but had played sparsely since Janevski took over, as part of the deal to bring defender Nemanja Pejčinović to Red Star. However, by February 2009, no trade had been announced by the teams, and he was still on the list Red Star players that started preparations for second half of the season. District of Columbia United
Lamar Hunt United States. Open Cup (1): 2013
Shimizu South-Pulse
Jakovic signed with Japanese club Shimizu South-Pulse on 14 January 2014.
Jakovic made his debut for senior Canadian men"s soccer team on 30 January 2008 against Martinique.
Later in 2008 he earned five caps for the Canada U-23 squad in the 2008 CONCACAF Men"s Pre-Olympic Tournament, during which Canada finished third, one place out of qualification. Jakovic was selected for the 2011 CONCACAF Gold Cup, however sustained a hamstring injury a week prior to the group stage in a friendly at BMO Field against Ecuador the match ended 2–2.
David Edgar was selected on 6 June, to replace Jakovic in the 23-man squad for the CONCACAF tournament.