In November 2017, he was named the Test batsman of the year for the 2016–17 season at Sri Lanka Cricket's annual awards.
de Silva started his cricket career at Deberawewa National School in Tissamaharama, Hambanthota.
[5] With the sudden death of his father, de Silva withdrew from the Sri Lankan squad for the West Indies tour.
[7] In March 2018, de Silva was named as the vice-captain of the Colombo squad for the 2017–18 Super Four Provincial Tournament.
[16] In July 2015, de Silva was named in Sri Lanka's Twenty20 International (T20I) squad for their series against Pakistan.
[19] In July 2016, de Silva was named in Sri Lanka's Test squad for their series against Australia.
[27] After Sri Lanka's Tillakaratne Dilshan retired from ODIs, de Silva was promoted to his slot of opening position.
His poor performances against South Africa had him dropped from the opening slot, but was played as a middle order batsman.
However, Kusal Perera was ruled out of the tournament with a hamstring injury, and de Silva was called up to the squad.
However, after strong performances in Test and ODIs, Dhananjaya was included to the one-off T20I against South Africa on 14 August 2018.
In the match, he showcased an all-round performance, with South Africa being bowled out for 99 runs, which was their lowest score in T20Is.
[38] In April 2019, de Silva was named in Sri Lanka's squad for the 2019 Cricket World Cup.
In the Boxing Day Test match, he scored his seventh 50 and strengthened the first innings along with Dinesh Chandimal.
[45] However, he retired hurt when on 79, after showing severe discomfort, collapsing to the ground, and had to be helped off the field and into the dressing room.
He batted for the entire fourth day, with Sri Lankan captain Dimuth Karunaratne, without losing a wicket and put on record breaking partnership.
[49] In September 2021, de Silva was named in Sri Lanka's squad for the 2021 ICC Men's T20 World Cup.
[52] On 1 November 2022, de Silva hit fifty and therefore Sri Lanka held a six-wicket lead over Afghanistan.
[55] Against Afghanistan in February 2024, he led Sri Lanka to the victory and win the one-off test series.