Olympic Games debut
1948 (London, England): Guyana, Jamaica, Trinidad and Tobago
1952 (Helsinki, Finland): Bahamas#
1968 (Mexico City, Mexico): Barbados, US Virgin Islands
1976 (Montreal, Canada): Antigua and Barbuda, Netherlands Antilles*
1984 (Los Angeles, USA): British Virgin Islands, Grenada
1988 (Seoul, South Korea): Cayman Islands, St. Vincent & the Grenadines
1996 (Atlanta, USA): Dominica, St. Lucia, St. Kitts and Nevis
2012 (London, England): Curacao*
Montserrat is set to compete for the first time in 2016.
Anguilla and Turks and Caicos have never sent a representative to Olympics as the territories do not have an Olympic Committee.
#Bahamas first competed in 1952 with a team of seven sailors. Athletes competed for the first time in 1956.
*Curacao athletes previous competed as part of the Netherlands Antilles. However, the Netherlands Antilles were dissolved in 2010 and became a part of the Netherlands. However, Curacao athletes competed under the IOC flag in 2012.
(Source-2016 Rio Olympics IAAF Hand book).