Domestic Career

In March 2018, he was named to Dambulla's roster for the 2017–18 Super Four Provincial Tournament. The following month he was also named to Dambulla's squad for the 2018 Super Provincial One Day Tournament.

In August 2018 he was called up to Galle's squad for the 2018 SLC T20 League.[5] In March 2019, he was named to Kandy's roster for the 2019 Super Provincial One Day Tournament. In October 2020, he was drafted by the Colombo Kings for the inaugural edition of the Lanka Premier League.

In March 2021, he was part of the Sinhala Sports Club team that won the 2020–21 SLC Twenty20 tournament, the first time they won the tournament since 2005.

International Career

He played in the tour match between the SLCB President's XI and Pakistanis in June 2015.

He made his Twenty20 International debut for Sri Lanka against Pakistan on 30 July 2015. He failed to take a wicket and ended with counts of 25 runs from 4 overs.

Vandersay made his One Day International (ODI) debut for Sri Lanka on 28 December 2015 against New Zealand as the 168th ODI player for Sri Lanka. He scored 7 runs, not in his first ODI innings, but at bowling he was hit badly by Martin Guptill and in the end Vandersey conceded 34 runs in 2 overs. Sri Lanka lost the match by 10 wickets. However, his first ODI wicket came during the 3rd ODI at Saxton Oval when he sacked Tom Latham for 42 runs.

He took his first Twenty20 International wicket by sacking Corey Anderson in the first Twenty20 International against New Zealand at the Bay Oval. Vandersay was originally included in the 2016 ICC World Twenty20 Sri Lanka squad, but was dropped from the World Cup squad due to poor performances on tours in New Zealand and Pakistan. He was later reinstated in the squad after Lasith Malinga was out through injury.

In January 2017 he was included in Sri Lanka's ODI squad for the series against South Africa.

In November 2017 he was included in Sri Lanka's Test squad, replacing Rangana Herath ahead of the third Test against India but he did not play. In May 2018 he was called up to Sri Lanka's Test squad for the series against the West Indies. He did not play in any matches and prior to the third and final Test of the series, he was sent home due to behavior issues.

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 December 2018, he was named to the Sri Lanka team for the 2018 ACC Emerging Teams Asia Cup.

On 23 June 2018, Vandersay was sent home by Sri Lanka Cricket (SLC) after breaching his player's contract over disciplinary issues. He was in the Caribbean at the time, but didn't play any matches. During the press release, SLC reported an "incident" that followed this decision. The following month he was sentenced to a year's suspended sentence and a fine equal to 20% of his annual contract.

In April 2019 he was called up to the Sri Lanka squad for the 2019 Cricket World Cup. In February 2022 he was called up to Sri Lanka's Test squad for the series against India. In June 2022, he was called up to the Sri Lanka A squad for their games against Australia A during the Australia tour of Sri Lanka. Later that month he was named in Sri Lanka's Test squad, including for their home series against Australia.