Domestic and T20 Franchise Career

In March 2018, he was named vice-captain of Kandy's squad for the 2017–18 Super Four Provincial Tournament. With 315 carries in three games, he was the leading run scorer for Kandy during the tournament. He was also named vice-captain of Kandy's squad for the 2018 Super Provincial One Day Tournament the following month.

In August 2018, he was called up to Galle's squad for the 2018 SLC T20 League. In March 2019, he was named to Dambulla's roster for the 2019 Super Provincial One Day Tournament.

In June 2019, he was selected to play for the Montreal Tigers franchise team in the 2019 Global T20 Canada tournament. In October 2020 he was drafted by Dambulla Viiking for the inaugural edition of the Lanka Premier League. In November 2021, he was selected by draft player for the 2021 Lanka Premier League to play for the Dambulla Giants.

International Career

He made his Test cricket debut for Sri Lanka against South Africa in July 2014. He made his One Day International debut for Sri Lanka against India on 16 November 2014. He made his Twenty20 International (T20I) debut for Sri Lanka against India 2016 on 9 February.

Dickwella was originally included in the ICC World Twenty20 Sri Lanka 2016 squad but due to poor performances in the 2016 India Tour and Asian Cup, he was dropped from the World Cup squad.

Dickwella was called up for the South African Limited Over Tour after performing well in national tournaments. He was drafted into the T20I team as the opening batter and hit fast innings in all three games. In the third game he scored his first T20I 50 as a match winner, ensuring the first consecutive win over South Africa on home soil in any format. Dickwella was named both Man of the Match and Player of the Series for his match-winning batting performances.

After the suspension, he was looking forward to returning to the squad for the second ODI against Bangladesh in late March 2017. However, due to a hairline fracture in his left hand, he was dropped from the series.

He scored his first ODI century on 6 July 2017 against Zimbabwe at Mahinda Rajapaksa International Cricket Stadium. They partnered with Danushka Gunathilaka for the first wicket on 229 runs, where Gunathilaka also scored his first ODI century. Sri Lanka chased 310 to win the match, which was Sri Lanka's first 300-plus pursuit on home soil. In the fourth ODI against Zimbabwe, he and Danushka Gunathilaka set the record of becoming the first pair of batsmen to score two consecutive partnerships over 200 in ODIs.

In May 2018 he was one of 33 cricketers to receive a national contract from Sri Lanka Cricket ahead of the 2018–19 season. In March 2021, during the first Test against the West Indies, he set a new record by scoring the most half-centuries by a batsman (17) in Test cricket without scoring a century, beating Chetan Chauhan's previous record .

Disciplinary Problems

In July 2014, on his Test debut, he was fined 10% of match fees for claiming an unfair catch.

During the fourth ODI against South Africa on 7 February 2017, Dickwella had a verbal encounter with Kagiso Rabada and was fined and given three demerits. On 21 February 2017, Dickwella was suspended for two limited-time games following a code of conduct violation during the second T20I against Australia at Kardinia Park. He was fined 30% of his match fees and received two more demerits.

In July 2017, Dickwella was fined 30 percent of his match fee and received two demerits for violating the ICC Code of Conduct. during the ODI against Zimbabwe.

On 28 June 2021, Sri Lanka Cricket (SLC) suspended Dickwella, Kusal Mendis and Danushka Gunathilaka after they breached the team's biosecure bubble during Sri Lanka's England tour. All three players were spotted in Durham city center and SLC sent them all home ahead of the ODI games. In July 2021, following the outcome of the incident, Dickwella was banned from playing international cricket for a year. Sri Lanka Cricket agreed to lift the ban early and have the punishment lifted in January 2022.

Awards

2012 Student Cricket Player of the Year
Dialog SLC Rising Cricket Player of the Year 2016-17.