Cleveland joined Austin FC on December 24, 2023 on a two-year guaranteed contract through the end of the 2025 MLS season, with an option for 2026. In his first season with Austin, Cleveland appeared in one (1) Leagues Cup match, saving a penalty kick in the 94th minute to preserve a 3-2 win over Liga MX side Pumas UNAM.
Cleveland entered MLS in 2017 when Chicago Fire FC selected the Ohio native in the second round of the MLS SuperDraft. Cleveland spent the first two (2) years of his professional career on loan at FC Tulsa (then Tulsa Roughnecks) of the USL Championship, while also making five (5) MLS starts for Chicago.
In 2019, Cleveland joined USL League One side Lansing Ignite on loan and kept seven (7) clean sheets in 22 matches to help guide the team to a second-place finish. Following the 2019 season, Seattle Sounders FC acquired Cleveland via trade.
Cleveland went on to post MLS career highs in starts (15), minutes played (1,350), shutouts (3) and saves (29) in 2021. Across four (4) total seasons in Seattle, Cleveland tallied four (4) clean sheets and 61 saves in 24 matches.
During his collegiate career, Cleveland played for three (3) years at Dartmouth College and picked up Ivy League Defensive Player of the Year honors in 2015. He transferred to the University of Louisville for his senior season, recording an 0.72 goals against average with the Cardinals.
