Clegg played at James Madison University from 2018-2022. Over the course of five seasons, he played a total of 5,270 minutes with 78 appearances.
In his sophomore season, he recorded a total of 902 minutes. Clegg’s most recognizable season was in 2021, where he was recognized as VaSID All-State Defensive Player of the Year, Defensive Player of the Week twice, and earned a spot in All-CAA First Team. During his senior year, he was recognized in the Sun Belt All-Tournament Team, where he made 19 appearances, recorded five goals, and one assist.
After completing his college career, Clegg made the leap to professional soccer. Clegg was signed to MLS Next Pro team Portland Timbers from 2023, where he made 46 appearances, played a total of 1,307 minutes. Clegg made two appearances for the first team at the 2023 Coachella Valley Invitational preseason tournament.
His most recent team was Sacramento Republic FC, where Clegg made one appearance for the Republic against the Switchbacks on March 22.