Jeff played at No. 3 singles for the second year in a row and compiled a winning record for the second straight time. Last season Jeff was 17-15 and as a freshman he was 18-13. Jeff played No. 2 doubles, primarily with Josh Lederman, and had an 18-13 mark. As a freshman, he went 4-5 in doubles playing mostly at No. 3. Before coming to Yale, Jeff won the Illinois State High School Singles Championship, and also won the Sportsmanship Award. In 2004, he finished with a top 50 national ranking in singles. He graduated fourth in his class at St. Francis High School.