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. In July 2000, the newly appointed Jamaica technical director of football, Clovis de Oliveria, decided to axe the five based British-based players, including Sinclair, from the upcoming 2002 FIFA World Cup qualifiers for "disciplinary reasons". However, Sinclair was later re-instated into the side and appeared in four qualifying matches in June and September 2001, but Jamaica failed to qualify for the World Cup after only winning two of their ten matches. It was two years before he made another appearance for the side and in August 2003 Sinclair stated that his appearance in the summer friendly against Nigeria would be "more than likely" his last appearance for Jamaica. He wanted to give the younger players a chance of breaking into the team and wished to focus on his club career with Leicester City, stating that the transatlantic travel could affect his form. In September 2003, he reversed his decision and was included in the squad for the friendly against Australia played at the Madejski Stadium in Reading, Berkshire. The friendly against Brazil in Leicester in October 2003 proved to be his final appearance for Jamaica, with Sinclair earning a total of twenty-eight caps. Managerial career Colwyn Bay After being appointed player-manager, Sinclair helped save Colwyn Bay from relegation and was named as Conference North Manager of the Month for April 2013 after overseeing six successive victories. He credited his success to new signings Shelton Payne and Jamie Ellison, as well as veteran midfielder Fraser McLachlan. He signed a new one-year contract in the summer. In July he convinced veteran striker Ade Akinbiyi to join the club. Sinclair was again named as Manager of the Month after winning all five matches in December 2013. He was named as the bookies favourite for the vacant Wrexham management post in February 2014. Sinclair led Colwyn Bay to a 12th-place finish in the 2013–14 season, the highest finish in the club's history. On 5 January 2015, he resigned as manager of Colwyn Bay, a day after a 5–0 defeat to Boston United which left the club 11 points outside the play-off places. He went on to work as a youth-team coach at Oldham Athletic. Brackley Town He featured "intermittently" for struggling Conference North side Brackley Town in the 2014–15