De Silva had his initial education at Isipathana College, Colombo before attending D. S. Senanayake College, Colombo.

A successful season playing first-class cricket for the English county Kent in 1995 marked a turning point in his career.

County cricket with Kent

Following the Sri Lankan tour of New Zealand De Silva joined the English county side Kent in April 1995 on short notice after Kent's leading batsman of the previous season, Carl Hooper, left to join the West Indies team for the summer. The season proved to be a mix of disappointment and success for Kent, as they finished last (18th) in County Championship with only three wins and four draws out of 17 matches played. Their form in the 40-overs National Cricket League was much better, and they finished on top of the league table with 12 wins, four losses and one abandoned match. In addition, Kent reached the final of Benson & Hedges Cup, where they lost to Lancashire by 35 runs despite de Silva's 112 runs. Personally for de Silva, the time spent with Kent marked the turning point in his career. He was the third most prolific batsman of the County Championship in 1995 after Mark Ramprakash and Nasser Hussain with 1661 runs at an average of 59.32 and six centuries including the highest score of the season, 255. He was also often called to perform as fifth or sixth bowler, a role where he proved to be relatively economic but inefficient wicket-taker.

De Silva did not play in Kent's two last County Championship matches having left to join the Sri Lankan squad on their tour of Pakistan.

On 28 July 2007 he made a one-off appearance for a friend for Dorset county league side Sherborne.

He made his Test match debut in 1984 at Lord's against England. During the early part of his career he was known as a dashing but inconsistent batsman – he was given the nickname "Mad Max" for his tendency to get out to rash shots. He later commented on his aggressive batting style: "That's my natural game – I don't want to change because I feel confident playing that way. If someone is capable of dominating the bowling, they should do it. It's the way I've been playing since I was a youngster."

De Silva was instrumental in Sri Lanka's triumph in the 1996 Cricket World Cup where his unbeaten century and three wickets earned him the Man of the Match award in the final against Australia. His other notable achievements include scoring a century in each innings of a Test match on two separate occasions (only bettered by India's Sunil Gavaskar,Australia's Ricky Ponting and David Warner, who each performed this feat three times). One of these doubles was 138 and 105, both unbeaten, against Pakistan at Colombo's Sinhalese Sports Club in April 1997. This made him the first, and so far only, player to score two unbeaten centuries in the same Test match. As he had