Chandana was considered to be one of the best leg spinners in Sri Lanka. 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 Bundaberg Rum Stadium in Cairns.