2008-2009: Champion along with doubles partner Ben Stein, of the NCAA Division III Men’s Tennis Doubles Championship, where they defeated Bowdoin doubles team, Jamie Neely and Oscar Pena in the finals (6-4, 5-7, 6-4). This was the second NCAA tennis crown overall (Will Boe-Wiegaard won the singles title in 2006) for Bates…. Named to All-NESCAC Honors for the second year in a row for doubles and singles; earning First Team honors for doubles with partner Ben Stein, and Second Team honors for singles…. Stein and Rupasinghe also won the Intercollegiate Tennis Association New England Championships earlier that year in late September of 2008, defeating Bowdoin pair Stephen Sullivan and Alex White. Their win at the ITA New England Championships earned them a bid and a number two seed in the ITA National Small College Championship in October, where the two finished in fourth place after being defeated by Washington University’s Charlie Cutler and Chris Hoeland 7-6(2), 6-4.
2007-2008: Made it to the doubles finals in the NCAA Division III Championships with teammate Benjamin Stein…. Named to Second Team All-NESCAC as both a singles player and as a doubles team player, along with Stein…. Rupasinghe and Stein teamed up to go 20-9 as Bates’ top doubles pair this year, achieving a No. 3 ranking in the Northeast, as determined by the Intercollegiate Tennis Association…. Went 15-10 playing singles for the Bobcats, most often at the No. 2 spot…. Bates went 9-0 against Babson in February; Rupasinghe and Ben Stein had an 8-2 victory at first doubles over Beavers Walt Sea and Ben Edick and Rupasinghe took care of Edick at NO. 2 singles, 6-0, 6-3…. Bates won 8-1 over MIT in March; Rupasinghe won at No. 2 singles and teamed up with Ben Stein to win at No. 1 singles…. Rupasinghe contributed to Bates’ 9-0 shutout over Brandeis in March as he won at No. 2 singles and teamed up with Ben Stein to defeat Brandeis’s Simon Miller and Scott Schulman in a hotly contested No. 1 doubles matchup, 9-8 (7)…. Against Colby in March, teamed up with Ben Stein to win 8-2 at No. 1 doubles.
2007: Played first and second singles and first doubles for the Bobcats…. Captured the national men’s singles title in his native Sri Lanka on August 19, defeating four-time runner-up Rajeev Rajapakse in straight sets, 7-5, 7-6, 6-0, in Sri Lanka’s 92nd annual national tennis tournament.