In October 1996, Bermuda were invited to compete in the Shell/Sandals Trophy, the West Indian domestic limited-overs competition. Making his List A debut, Smith scored a total of 151 runs at the tournament, behind only Charlie Marshall for Bermuda. His tournament included half-centuries in the opening two games – 52 against the Windward Islands and 69 against Barbados. Both Smith and the team as a whole had little success at their next major tournament, the 1997 ICC Trophy in Malaysia. Smith scored only 126 runs from six innings (with a highest of 43 not out against Italy), while Bermuda failed to make the tournament's second round, placing ninth overall (after a fourth-place finish at the previous edition). Later in 1997, Smith represented Bermuda in the 1997–98 Red Stripe Bowl (the renamed Shell/Sandals Trophy). In the second match of the tournament, against the Windward Islands, he scored 100 not out, the first List-A century by a Bermudian. Two matches later, against Jamaica, he scored 101 not out, though neither of his innings were enough to secure his team a win.