2019-20 Season (Senior) - In his final season with Lees-McRae in 2019-20, Caldwell posted a 1-0 singles record and a 2-3 doubles mark...Caldwell won his lone singles tilt from the No. 5 position...In doubles, he mainly teamed with Colton Porter and the duo went 2-1...He also teamed up with Matt Meluch and Harrison Morris in one match each...After the season, Caldwell was named to the All-Conference Carolinas team by the league office. 

2018-19 Season (Junior) - Caldwell posted three doubles wins with Colton Porter at No. 3 doubles, while also winning two matches at No. 5 singles on the season...He and Porter earned a 6-4 win against Milligan on Feb. 23, while picking up a 6-1 win against the University of Scranton on Mar. 11...The duo also earned a 6-4 win against Southern Virginia on Mar. 13...Caldwell swept his Johnson C. Smith opponent 6-4, 6-3 on Feb. 24, before posting a 6-2, 6-0 win against the University of Scranton on Mar. 11.

2017-18 Season (Sophomore) - In his second season at Lees-McRae, Caldwell went 2-12 in singles and doubles action in 2018...Playing all of LMC's matches out of the No. 5 singles and No. 3 doubles spots, Caldwell picked up singles and doubles victories in matches against UVa-Wise and Erskine on the season...After the season, Caldwell was named to the Conference Carolinas Presidential Honor Roll. 

2016-17 Season (Freshman) - Caldwell posted an 1-13 record as a singles competitor and a 0-12 doubles mark...Caldwell's first career singles victory came over Greensboro College's Warren Washington.