Born in Libertyville, Illinois, Hollingsworth attended Libertyville High School. He was a three-year varsity starter for the Wildcats and was twice named IHSA All-State. As a junior in 2010, Hollingsworth led the Wildcats to a state runner-up finish, losing in the 3A championship game to Boylan Catholic High School. His senior season, Libertyville won the Pepsi Showdown over Lyons Township High School, as well as a regional championship, but were knocked out in the sectional semifinals by Fremd High School. Hollingsworth was named IHSA All-Midwest and was named as the Lake County All-Area Captain his senior season.
