He has coached Everest Premier League side Bhairahawa Gladiators, and the national teams of the United States, Canada, and Nepal.
He spent just over a year as Sri Lanka's first-choice wicket-keeper, with his last international matches coming on a 1994 tour of New Zealand.
[2] 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.
[6][7] 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.
At the 1994 Austral-Asia Cup in the United Arab Emirates, Dassanayake played ODIs against Australia and New Zealand for the first time.
This was followed by the Singer World Series (a quadrangular ODI tournament hosted in Sri Lanka), and then by a tour of Zimbabwe.
[6][7] Dassanayake played his final international matches in December 1994, at the Mandela Trophy (a one-off ODI tournament hosted in South Africa).
[7] 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.
[2] 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.
[11] Later in the year, Dassanayake represented Canada in ICC Intercontinental Cup matches against Bermuda and the Cayman Islands, serving as captain in the absence of John Davison.
In October 2015, Dassanayake stepped down as Nepal coach, citing personal reasons, ending his four-year tenure in the role.
[16] In September 2016, it was announced that Dassanayake had won the position, with his first major tournament in charge to be the 2016 World Cricket League Division Four event in Los Angeles.