In 2010, he made 24 appearances and scored five goals, including a game winner in the NCAA College Cup final against Louisville to capture the school's first ever national title in any sport.
[3] He also recorded an assist that year and was named Most Outstanding Offensive Player at the College Cup and Academic All-MAC.
During his college years, Caldwell also played in the USL Premier Development League for the Michigan Bucks, the Central Jersey Spartans and the Akron Summit Assault.
[9] He recorded his first career assist on June 29, 2013, setting up Chad Barrett's equalizing goal in a 1-1 draw with Chivas USA.
[10] Caldwell scored his first MLS career goal on April 25, 2015, the fourth in the Revolution's 4-0 win over Real Salt Lake.