He made his first-class debut in January 1999, opening the batting for the Windward Islands in a Regional Four Day Competition match, he made low scores of 12 and 4 in a heavy defeat to Barbados. His first half-century was brought up in his third match of the season, scoring 79 in the first innings against the Leeward Islands. It was the only time he passed 50 runs in his debut season, finishing with a batting average of 18.44 from nine innings, which is considered low for a specialist batsman. His average remained around that level over the following two seasons. Despite his relatively low scoring, he was picked to play for the West Indies A team against South Africa A in September 2000, making scores of 14 and 23 in a drawn match. In the 2000–01 season Smith was part of the Windward Islands team that won the List-A West Indian domestic competition for the second time in their history.