Calvert officially added Boys' Tennis to the sports curriculum in 1969. In the spring of 1973, under the leadership of Coach Jack "Sparky" Anderson, the program recorded its first league title (SBC). "Sparky" continued in his post until his sudden death in 1987. In 1988, Coach Dave Kimmet took over, and in 1990 his team recorded an undefeated season with a total of 17 wins. Coach Kimmet's 1993 team duplicated the feat as well, as they produced 14 wins. Coach Kimmet continued in the post through the 2009 season, and was succeeded by Coach Karen Kapelka-Kwiat. Coach Kapelka-Kwiat led the program through the 2013 season before stepping down.
Coach Alex Lucius led the program during the 2014 season, followed by Robbie Ball in 2015. Coach Sarah Herald began her tenure as head coach beginning in the spring of 2016, and is currently leading the program today.