2019 (Lansing Ignite FC): Started all 22 of his appearances while on loan with USL League One club Lansing Ignite FC, totaling 1,980 minutes. Cleveland allowed 26 goals and made 67 saves while posting seven shutouts.
2018 (Chicago Fire FC): Cleveland started all five of his appearances in MLS regular season play and totaled 450 minutes. He allowed eight goals and made 25 saves while posting a 1-3-1 mark for Chicago. Cleveland earned his first career victory on September 29, 2018 when he made five saves in a 3-1 win vs. LAFC.
At Louisville, Cleveland appeared in 22 games for the Cardinals in 2016 and earned 10 shutouts en route to a 0.72 goals against average. He spent his first three collegiate seasons at Dartmouth, where he appeared in 33 games and earned 16 shutouts, and was named 2015 Ivy League Defensive Player of the Year.