After earning an engineering degree from Dartmouth College in 2016, Cleveland began graduate school at the University of Louisville in 2017.

[5] He made his professional debut on May 27, 2017, whilst on loan with Chicago's United Soccer League affiliate Tulsa Roughnecks during a 3–1 win over Portland Timbers 2.

[6] He made his MLS debut on August 4, 2018, starting in a 2–1 loss to Real Salt Lake, making 8 saves and allowing 2 goals.

[8] He has mainly played for reserve team Tacoma Defiance or filled in for starting Sounders goalkeeper Stefan Frei during congested weeks of the season or with injuries.

[10] On December 24, 2023, Austin FC acquired Cleveland as a free agent and signed him to a two-year deal with a club option for the third year.