Calvin had a very successful freshman campaign. He led the team in singles wins with 20 playing mostly in the #4 & #5 positions. He played #1 doubles for most of the year, and had a winning Ivy League record in both singles and doubles.
Prior to Yale, Calvin finished the 2006 season ranked #54 nationally in singles, and he and his partner were ranked #3 in the nation in doubles in the 18 & Under division. The highlight of their season was winning the USTA Spring National Championships in Mobile, Alabama. Calvin was the captain of his high school team at The Waterford School and won the state championships 4 years in a row. Calvin is a multiple sportsmanship award winner throughout his junior career.