sinclair was included in the jamaica squad at the 1998 fifa world cup held in france, making history as they became the first english-speaking caribbean country to qualify for a world cup. he started in all three group matches against croatia, argentina and japan. jamaica lost the opening two games but claimed their first ever points at a world cup with the 2–1 victory over japan in lyon, but were still eliminated finishing third in the group. over the next couple of years sinclair represented the side in a number of friendly matches and was included in the squad for the 2000 concacaf gold cup. he played in the two group stage matches, a 1–0 defeat to colombia and 2–0 defeat to honduras as jamaica were knocked out at the first stage.