On February 15, 2018, Hollingsworth scored a freshman season-high 30 points, the most by a Western Kentucky freshman since 1955,[7] and grabbed seven rebounds in a 102–94 overtime win over North Texas.[8] On March 21, he scored 30 points for a second time with eight rebounds in a 92–84 quarterfinal win over Oklahoma State at the 2018 National Invitation Tournament.[9] As a freshman, Hollingsworth averaged 13.3 points, 3.4 rebounds and 1.9 assists per game despite playing several games with a broken nose. He earned Conference USA All-Freshman Team honors and surpassed Courtney Lee for Western Kentucky's freshman scoring record.[10] Hollingsworth was suspended from an exhibition game prior to his sophomore season for a violation of team rules, after being cited for marijuana possession.[11] As a sophomore, he averaged 14.4 points, 4.4 rebounds and 2.2 assists per game. He was named to the Third Team All-Conference USA as well as the All-Tournament Team.[12]
On February 27, 2020, Hollingsworth posted a career-high 43 points, six rebounds and three assists in a 95–91 overtime win over Louisiana Tech. He scored the most single-game points by a Western Kentucky player since Jim McDaniels in 1971.[13] Five days later, he was named Oscar Robertson National Player of the Week.[14] As a junior, Hollingsworth averaged 16.6 points, 4.2 rebounds and 2.7 assists per game, earning First Team All-Conference USA honors.[15] He averaged 13.9 points, 3.8 rebounds and 2.4 assists per game as a senior and was named to the Second Team All-Conference USA. Hollingsworth announced he was turning professional rather than use the fifth year of eligibility granted due to the COVID-19 pandemic. He finished his career fifth on Western Kentucky's all-time scoring list with 1,896 points, set the school record with 131 games started, and ranked in the top 10 in career steals, free throws made, free throws attempted and free-throw percentage.[16]
Hollingsworth is the son of Kathy Sweatt and Maurice Hollingsworth. Both of his parents were standout basketball players at Harlan High School in Harlan, Kentucky.[1] He has a daughter, Aubrey, who was born in 2017.[19]