Boskovic made three appearances for Toronto FC II during the 2015 USL season, after being rewarded with a call-up from the TFC Academy.

[5] On March 6, 2019, it was announced that Boskovic would be loaned to USL Championship club Ottawa Fury FC for the 2019 season.

[7] On March 11, 2020, Boskovic re-signed with Toronto and was subsequently loaned to Canadian Premier League side Cavalry FC for the 2020 season.

[13] In the early stage of the season, he helped the Serbs win the Royal CSL Cup against Scarborough SC.

[15] Boskovic was named to the Canadian U-23 provisional roster for the 2020 CONCACAF Men's Olympic Qualifying Championship on February 26, 2020.