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Despite having lost its top three players to graduation following its third straight winning campaign (11-10 in 1997-98), the 1998-99 Wesleyan men's squash team was not expected to use the season as a foundation for rebuilding. Interim head coach Don Long felt his troops would step right up and continue the winning ways. What he got was more than expected as the team tied the record for most wins in a season with 13, done previously in 1979-80 (13-9) and set a team mark for winning percentage (.650) by posting a 13-7 record. At the national team tournament, hosted by Harvard, Wesleyan finished 14th among 38 teams.

Moving up from the no. 4 slot a year ago was Dave Ross '00, who split time with newcomer Colin Hawes '02 at no. 1. Playing the bulk of the matches at the top two spots on the ladder, these two combined for an 18-19 mark . Two other frosh, Olm Pandejpong '02 and Taylor Greene '02, were major factors in the Cardinals' success as they played in the bottom half of the ladder with a collective 28-10 record. Ari Gerzon-Kessler '99, who was named a scholar-athlete by the National Intercollegiate Squash Racquets Coaches Association (NISRA), had a 12-7 record, mostly at no. 6, and a three-year varsity record of 31-20. Evan Jenkins '01 also had a solid record, going 14-6 overall, mostly at no. 7.

The team again graduates three regulars from the lineup, leaving a strong nucleus of players to extend the winning tradition to a fifth consecutive year. In 1995-96, when Wesleyan began the streak with a 12-11 mark and an 18th-place finish at nationals, the team received the Barnaby Award, presented annually to the most improved team in the country. The year before, Wesleyan had gone 5-12 and finished 24th nationally.