Boys Interscholastic Tennis at Andover dates back to 1884. Andover won the singles match and lost the doubles.
Between 1890 and 1921 the Andover-Exeter series resulted in 13 Exeter wins, 13 Andover wins and 5 ties. In 1922 and 1923, captained by Charles Watson, III, Andover won the Interscholastics, hosted at Harvard. Watson was the fifth-ranked junior in the country at the time, and he played Bill Tilden, then number one player in the world, at Andover in an exhibition match, losing 6-3, 6-2, 6-2. Narrowly beaten by Exeter 5-4 the following year, Andover came back under the captaincy of Frank Luce and won for three years running, the 1925 team going undefeated. Captain Charlie Sturtevant played future Wimbledon champion Frankie Shields at the 1927 Interschols, taking him to three long sets. Shields, now better known as the grandfather of Andre Agassi's first wife, Brooke, was then the national junior champion. The 1928 and 1929 teams won the Interschols in Cambridge, captained by Wingate Paine, and for the next five years Andover won twice handily but had to come from behind three times against Exeter for 5-4 wins. Captains were Barclay Kingman, Harry Thompson, Jack Malo and Hobe Early.
Between 1953 and 1956, Andover was led by Robert Semple and Maitland Jones. The 1956 team won the Interscholastic title under the captaincy of Lowell Latshaw. A strong 1959 team captained by Kirby Jones included David Smoyer, Whit Foster, Nick Saxton, John McPherson and Carl Forsythe, coached by former Dartmouth player Charles Dey of the History Department. During the years 1961 to 1971, Andover never lost to Exeter. The 1962 team was captained by George Andrews, and in the following years standouts were Jack Morrison, José Gonzalez, Steve Devereux, Farlow Blakeslee, John Spiegel, Erich Wise, Bill Mears, Stuart Lytel, Rick Devereux, Gavan O'Herlihy, John Clauss, Hugh Peck, David McCracken, Peter Blazier, Grant Heidrich and John Bush. In more recent years, John Niceforo, Tim Clark, Peter Palandjian (eventual Wimbledon player), Rob Cantu, Moustapha Diop, Chi-Wai Lam, Tom Reifenheiser, Ousmane Diop, Mike Shin, Dean Chiungos, John Hugo, Greg Chang, and Trey Meyer have earned particular distinction, the last three playing for Middlebury, St.Joe’s/UNC and Williams, respectively. Meyer was the 2009 NEPSAC Boys Tennis MVP.
Through the years, alumni matches have been particularly enjoyable. After Chi-Wai Lam led the 1989 team to Interschols victory, the 1990 team, captained by Jon Karlen, and led by Reifenheiser and Lam, won both the Kingswood Invitational Tennis Ttournament and Interschols. It was one of the best Andover teams ever, but the alumni were vindicated when Rob Cantu, `85, came back to Andover fresh from a satellite circuit and beat both Reifenheiser and Lam in two exihibition sets. Reifenheiser (twice) and Lam both were NEPSITT singles champions.