Chandana was considered to be the best leg spinner ever played for Sri Lanka. After him, there was no such effective leg spinner came to the side, only Malinga Bandara and Seekkuge Prasanna become successful in later stages. He was also a competent lower-order batsman, having scored a total of seven half-centuries at international level. He had two main variations in his bowling: a leg break and a googly.
Upul Chandana started his cricketing carrier as a teenager at Mahinda College, Galle. Despite making his ODI debut in 1994 aged 21, Chandana had to wait for five years to be included in the Test team. It came in the Asian Test Championship Final in March 1999 against Pakistan. Chandana bowled 47.5 overs in the first innings and finished with 6 for 179.
Over the next few years he made sporadic appearances for Sri Lanka and in 2002 he was named as captain of Sri Lanka A. They played an unofficial Test series against Kenya and Chandana topped both the batting and bowling averages. This helped him work his way back into the side in 2003 and after a match-winning innings against West Indies at Bridgetown, he became a regular player in the one day team. Chasing 313 for victory, he was promoted up the order to 5 and smashed 89 off just 71 deliveries with 6 sixes.
When Muttiah Muralitharan withdrew from the 2004 tour to Australia, Chandana came into the Test side as the main spin bowler. Despite being expensive, he took a ten wicket haul in the 2nd Test at Cazaly's Stadium in Cairns.
Chandana has played cricket in England for Gloucestershire County Cricket Club and represented Nondescripts in Sri Lankan domestic cricket. Chandana retired from Test cricket on October 15, 2007 and then joined the Indian Cricket League, playing for the Kolkata Tigers and ICL World XI. He with four other Sri Lankan cricketers were banned due to the involvement for ICL in 2008, but the decision was lifted on 2009, where they were able to play for Sri Lanka again in international cricket. Chandana was selected for Bangladesh tour in Sri Lanka in 2009. He retired from all international cricket with this tournament.
Jayasuriya has influenced for many international awards in his 20 years of cricketing career. He is second only to Sachin Tendulkar by the number of Man of the match awards for ODIs, where Tendulkar has 62 Man of the Match awards, and Jayasuriya has 47 of them. He also has 11 ODI Man of the Series awards. Besides ODI awards, he has 4 Test Man of the Match awards and single Test Man of the Series awards. He has 5 T20I Man of the Match awards as well.