Sri Lanka

Dassanayake was born in Kandy, in Sri Lanka's Central Province. A wicket-keeper, he made his first-class debut in January 1990, aged 19, playing for the Colts Cricket Club during the 1989–90 season of the Lakspray Trophy. Dassanayake switched to the Bloomfield Cricket and Athletic Club for the 1990–91 season, but played only a single limited-overs game. He appeared in another four one-day games the following season, playing twice for Bloomfield in the Hatna Trophy and also twice for the Sinhalese Sports Club in the Premadasa Trophy. Beginning in mid-1992, Dassanayake began to be selected for representative teams, playing first-class tournaments for Central Province and a Sri Lankan under-23s team. He toured Bangladesh with Sri Lanka A in December 1992, and the following month toured South Africa with a Sri Lankan under-24s side.

Leapfrogging Ashley de Silva and Romesh Kaluwitharana (the two wicket-keepers used in Sri Lanka's previous series) for selection, Dassanayake made his international debut in August 1993, playing three Tests and two ODIs in a home series against South Africa. Prior to the first Test, he had impressed selectors by recording six dismissals in an innings in a warm-up game for a Sri Lanka Board XI. After his debut series, Dassanayake's next international was a one-off Test against the West Indies in December 1993. The following month, he was selected for a tour of India, playing in three Tests and one ODI. At the 1994 Austral-Asia Cup in the United Arab Emirates, Dassanayake played ODIs against Australia and New Zealand for the first time. His next internationals came in a home series against Pakistan in August 1994. This was followed by the Singer World Series (a quadrangular ODI tournament hosted in Sri Lanka), and then by a tour of Zimbabwe.

Dassanayake played his final international matches in December 1994, at the Mandela Trophy (a one-off ODI tournament hosted in South Africa). He was unable to maintain his batting at the standard required for international competition, averaging just 13.06 across eleven Tests and 10.62 across sixteen ODIs. In his first domestic season after being dropped from the national team, Dassanayake scored two first-class centuries, including a career-high 144 for Bloomfield against the Panadura Sports Club.^[9] Although he never returned to the senior Sri Lankan team, he did play several more series for Sri Lanka A, appearing against the United Arab Emirates and India A in December 1995, against Bangladesh and Pakistan A in February 1997, and against England A in February 1998. His domestic career with Bloomfield ended after the 2000–01 season.^[3][4]

Canada

Dassanayake immigrated to Canada in