Cal Djuraskovic is in his first professional season with Windy City in 2021. He signed as a free agent on July 20, 2021 following a five-year collegiate career at Division II Davenport University. Cal also had a brief stint with the Gary SouthShore Railcats for whom he appeared in three games, including one start, and threw four total innings.

At Davenport, Djuraskovic went 6-4 with a 4.04 ERA, primarily as a reliever. He enjoyed his best season as a redshirt senior in 2021, when he pitched in 25 games and posted a 2.62 ERA with eight saves. He struck out 61 hitters and walked only 16 in his career-high 44.2 innings on his way to being named First Team All-Great Lakes Intercollegiate Athletic Conference. Prior to Davenport, he attended high school at the Bishop Noll Institute in Hammond, Indiana.