2018: New York City FC drafted Jeff Caldwell from University of Virginia on January 19, 2018 and then signed him on February 28, 2018 after a successful preseason training.
2014-2016: Jeff enrolled early at UVA in 2014 where he made his start against Old Dominion where he recorded a clean sheet. He started and played every minute of all matches in the 2015 and 2016 seasons and earned back to back All-ACC honors. Jeff has played with United States U-17 and U-18 national teams and was called to US U-20 National Team for training camp in Argentina. He made one U-20 cap in 2015 against England and was made a member of United States roster at 2015 FIFA U-20 World Cup.