Boskovic, 19, has made 25 appearances in three seasons for TFC II in the USL as a call up from the Toronto FC Academy. He made his debut for TFC II when he came on as a substitute against AS Roma Primavera on Tuesday, July 28, 2015. Boskovic made his USL debut on August 15, 2015 against the Richmond Kickers and earned his first start in USL on September 9 against the Charlotte Independence. In 2017, he also represented Toronto FC III at the 69thViareggio Cup, appearing in all three group stage matches.
Boskovic also played the past two seasons with the Ryerson Rams of the Ontario University Athletics (OUA). With the Rams, he appeared in 27 matches registering two goals and three assists. During his rookie season in 2016-17, he was named an OUA East Division first-team all-star, the OUA rookie of the year, a U Sports first-team all-star and the winner of the Lou Bilek Award for the U Sports men’s soccer rookie of the year. Boskovic is the first Ryerson Ram to claim the Lou Bilek award since its inception in 1999.