Scott Caldwell began his career at the University of Akron, helping to win the school's first National title. During his sophomore year, he was named the Most Outstanding Player at the College Cup and was awarded the Academic All-MAC. After receiving the accolades of All-America Scholar Player of the Year and Soccer America MVP First Team during his senior year, Scott landed himself a spot in the USL Premier Development League. In 2012, Caldwell signed his first MLS deal with the New England Revolution, naming him the second Homegrown Player in club history. Caldwell received high honors in 2015 when he was recognized as the New England Revolutions Most Valuable Player.