Coach Cleveland was born and grew up in Arlington, MA. He started to play lacrosse in fifth grade, and played for the local Arlington teams until he joined the Clams in the summer going into his junior year at Arlington High school. After a couple of seasons with the clams, Coach Cleveland decided to transfer to The Rivers School, where he repeated his junior year.
At Rivers, Coach Cleveland a two time member of the varsity lacrosse team. In lacrosse, he was a two time ISL All-star selection at the attack position. In the fall of his second Junior year, Coach Cleveland committed to Colgate University to play lacrosse for the Raiders in the Patriot League.
As a member of the Colgate Men’s lacrosse team, Coach Cleveland started all but two of all of the games during his time there, and was the team leader in points for 4 years in a row. Playing as a midfielder for the first time in the spring of 2018, Coach Cleveland was awarded an All-Patriot league selection for the first time. He currently sits 4th all time at Colgate in career assists (80) and has a career total of 144 points,
Coach Cleveland was a coach for the Littlenecks in the summers of 2015, 2016, and 2017.