Sinclair akabatanidzwa muchikwata cheJamaica paFIFA World Cup ya1998 yakaitirwa muFrance, ichiita nhoroondo sezvo vakava nyika yekutanga inotaura Chirungu muCaribbean kukwanisa kuenda kuWorld Cup. Akatanga mumitambo yose mitatu yeboka neCroatia, Argentina neJapan. Jamaica yakarasikirwa nemitambo miviri yekutanga asi yakawana mapoinzi avo ekutanga muNdebe yeNyika nekukunda Japan ne2x1 muLyon, asi vakaramba vachibviswa vachipedza vechitatu muboka. Mumakore maviri akatevera Sinclair akamiririra divi mumitambo yakawanda yeushamwari uye akaverengerwa muchikwata che2000 CONCACAF Gold Cup.
. Akatamba mumitambo miviri yechikamu cheboka, 1<unk>0 kukundwa neColombia uye 2<unk>0 kukundwa neHonduras sezvo Jamaica yakadonhedzwa muchikamu chekutanga.