Nov. 7, 2008 Trinidad and Tobago 3 – 1 Saint Kitts and Nevis Oct. 10, 2004 Trinidad and Tobago 5 – 1 Saint Kitts and Nevis Sept. 4, 2004 Saint Kitts and Nevis 1 – 2 Trinidad and Tobago Aug. 2, 2003 Saint Kitts and Nevis 1 – 2 Trinidad and Tobago Nov. 15, 2002 Trinidad and Tobago 2 – 0 Saint Kitts and Nevis

May 28, 1998 Saint Kitts and Nevis 4 – 1 Trinidad and Tobago July 13, 1997 Trinidad and Tobago 4 – 0 Saint Kitts and Nevis July 8, 1997 Saint Kitts and Nevis 0 – 3 Trinidad and Tobago May 28, 1996 Trinidad and Tobago 5 – 1 Saint Kitts and Nevis May 30, 1993 Trinidad and Tobago 3 – 2 Saint Kitts and Nevis