Jakovic took up soccer in Canada. He was a four-year letterwinner at Scarlett Heights Academy, and was named team MVP as a junior and senior, captaining both indoor and outdoor teams. He played in the Canada national youth program, and also for two-time Ontario Cup winner Woodbridge Strikers under Bob Graham. He was a member of the team that competed at the 2004 Dallas Cup, played with former UAB teammate Lukasz Kwapisz.[6]
At the age of eighteen, Jakovic had a trial with OFK Beograd, but was not signed by the team.[7]
On 28 June 2008, soon to be twenty-three-year-old Jakovic joined Red Star Belgrade ahead of the 2008–09 season, after successfully completing a tryout with the team.[11] He officially signed with the club on 30 June 2008.[12]
Jakovic made three league starts at the beginning of the season under head coach Zdeněk Zeman. However, following a 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.
At the 2008-09 winter break, Red Star began looking at options to move Jakovic. In December 2008 it was reported 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 a deal to bring defender Nemanja Pejčinović to Red Star.[13] However, by February 2009, no trade had been announced by the teams, and Jakovic was still on the list Red Star players that started preparations for second half of the season.[14]
D.C. United
Jakovic in 2012
Jakovic signed for Major League Soccer side D.C. United on 27 February 2009.[15] Jakovic scored his first goal for the club on 26 May 2012 against New England Revolution, the game ended in a 3–2 home victory.[16] Jakovic signed a contract extension with D.C. United following the 2012 season.[17]
Shimizu S-Pulse
Jakovic signed with Japanese club Shimizu S-Pulse on 14 January 2014.[18] Jakovic was released by Shimizu S-Pulse on 5 February 2017.[19]
Jakovic returned to the top flight when he signed with MLS expansion club Los Angeles FC in January 2018.[21] Jakovic would make his LAFC debut against Seattle Sounders FC during the 2018 season opener.[22] He re-signed with Los Angeles in January 2019 ahead of the 2019 MLS season.[23]
He moved on loan to Las Vegas Lights on 7 June 2019.[24] He was recalled three weeks later on the 28th.[25] Jakovic's option for the 2020 season was declined by Los Angeles, but he signed a new contract with the club in December 2019.[26][27]
Forge FC
On 13 May 2021, Jakovic signed with defending Canadian Premier League champions Forge FC.[28] He was limited to appearing in only five matches due to injury and left the club after one season.[29][30]
Serbian White Eagles
Jakovic returned to the Canadian Soccer League for the 2022 season to sign with the Serbian White Eagles.[31][32] He made his debut on June 26, 2022, against the Toronto Falcons.[31] He helped the Serbs in securing the regular-season title including a playoff berth.[33] In the second round of the postseason Jakovic served as the team captain where the Serbs were eliminated from the competition after a defeat to FC Continentals.[34]
Jakovic made his debut for the 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 also chosen in the 23-man roster for the 2009 CONCACAF Gold Cup;[35] Canada won Group A with 7 points before being knocked out by Honduras in the quarter-finals.[36]
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.[37]
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