Born on December 14, 1979 in Panadura, Chamara Silva comes from the old school of batting. He was a beneficiary of the youth policy adopted by Siddath Wettimuny in 1999 as he debuted against the visiting Australians in the Aiwa Cup at the tender age of 19. He began promisingly though with a half-century. His batting has drawn comparisons with the great Aravinda de Silva especially his low legged stance.
It was a struggle though for the flamboyant batsman as he struggled to find a permanent place in the Sri Lankan squad. His strong performances at the domestic level finally caught the eyes of the then Sri Lankan coach, Tom Moody.