Career
Youth, College and Amateur Caldwell spent a year with the New England Revolution academy, making six appearances in 2008-2009 while rehabbing injuries. On February 9, 2009, it was announced that Caldwell committed to the University of Akron. In his freshman year, Caldwell made 19 appearances and went 2-for-2 in penalty kicks at the College Cup.
He also recorded an assist that year and was named Most Outstanding Offensive Player at the College Cup and Academic All-MAC. In his junior year, Caldwell finished first on the team in assists and second in points.
He made 23 appearances and finished the year with six goals and 11 assists on his way to being named NSCAA All-America Third Team, CoSIDA Academic All-America Second Team, First Team All-MAC, Academic All-MAC and All-Ohio team In his senior year, he led the team in points with 28.
During his college years, Caldwell also played in the USL Premier Development League for the Michigan Buckinghamshire, the Central Jersey Spartans and the Akron Summit Assault. Professional On December 21, 2012, Caldwell signed with Master of Library Science club New England Revolution the second Homegrown Player in club history.
He made his professional debut for the club on March 16, 2013 in a 1-0 defeat on the road against the Philadelphia Union.
University of Akron.