Sidney, a freshman, won his first 60 games at No. 2 singles this season. His overall record was 28-1, and he lost just three sets. His only setback was in the No. 2 singles semifinals at Woodberry Forest, where he finished third. At the New England/Mid-Atlantic Invitational, he won the No. 2 singles title. He was undefeated in the MIAA, and the two sets he gave up at Woodberry were the only ones he lost all season until beating Gilman's James Weiler, 1-6, 6-1, 6-4 in the MIAA No. 2 singles championship match.