With four state championship teams and multiple singles and doubles titles to its credit, boys tennis is one of the most decorated programs in Saint Stephen’s athletics history. The Falcons have captured 16 district, seven regional, and four state crowns – the first in 1986 and their most recent in 2015.

The program has produced a long list of highly successful collegiate and professional players, counting among its alumni former world No. 1 Jim Courier. During his lengthy pro career, Courier won four Grand Slam singles titles – two at the French Open and two at the Australian Open. He holds the record as the youngest player to reach the finals of all four Grand Slam singles tournaments. Courier captured 23 singles and six doubles titles during his career. He spent 58 weeks ranked No. 1 and was inducted into the International Tennis Hall of Fame in 2005. As a Falcon, Courier earned a state championship in 1986.

Courier’s former SSES classmate and ’86 state champion teammate David Wheaton won the U.S. Open junior title in 1987 and was ranked the No. 1 junior player in the USA. In 1988, he enrolled at Stanford and helped the Cardinal win the NCAA Division I title. Wheaton was ranked as high as No. 12 as a singles player, reaching the Wimbledon singles semi-finals and the doubles finals at the Australian Open in 1991.

A third distinguished member of the 1986 Falcons was Martin Blackman, who joined Wheaton at Stanford and won a pair of NCAA Championships. He went on to play at the ATP level from 1989 to 1995. Blackman entered the coaching ranks in 1998 at American University and was a three-time conference Coach of the Year during his tenure. In 2015, he was named general manager of player development for the USTA, where he is responsible for partnering with the U.S. tennis community to identify and develop the next generation of world-class American players. 

Recent teams have continued the tradition of outstanding tennis at SSES. The 2019, 2021 and 2022 Falcons (the 2020 season was cancelled due to the COVID-19 pandemic) won consecutive district and regional titles, and advanced all the way to the Class 1A state championship match before finishing as state runner-up each time. From 2019-22, SSES posted a 46-4-1 record in dual matches, with three of those four defeats coming in the state finals. The 2023 Falcons won a district title but fell short of returning to the state tournament for the fourth straight season. However, the doubles team of Max Pettingell and Ricardo Perazzolo won their way to a berth in the state finals before falling just short.

Saint Stephen’s is coached by Scott Shields, who was one of the Sarasota-Bradenton area’s most decorated junior players during the 1980s, achieving a top 10 USTA ranking in Florida. A Bayshore High alumnus, he reached a junior ranking as high as No. 12 in the nation. Shields played collegiately at Florida State and earned an NCAA ranking of No. 27 as the Seminoles’ No. 1 singles player during his sophomore and junior seasons. He was a four-year starter during his career at FSU and won two conference singles and doubles titles.