He was a part of the Sri Lankan squad which won the 1996 Cricket World Cup, however he did not play any matches during the tournament.

Despite making his ODI debut in 1994 aged 21, Chandana had to wait for five years to be included in the Test team.

This helped him work his way back into the side in 2003 and after a match-winning innings against West Indies at Bridgetown, 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.

[3][4][5] Upul Chandana has the record for the highest test score when batting at number 9 for Sri Lanka(92).