He was educated at
Nalanda College Colombo. Rupasinghe was
OBSERVER-BATA Schoolboy Cricketer in 2006 and also became the best all-rounder in 2006. He captained Nalanda College's first XI team in 2006. Rupasinghe played for Sri Lanka School's under-17 team, at the Asian Schools Cricket Tournament, held in Sri Lanka in 2002; and toured with the Sri Lanka under-19 cricket team to Pakistan in 2005. He was included to the
2004 Under-19 Cricket World Cup Squad as well. In November 2021, he was selected to play for the
Colombo Stars following the players' draft for the
2021 Lanka Premier League. ==References==