2 Miss Universe winners are from Trinidad & Tobago:
1977: Janelle Commissiong
1998: Wendy Fitzwilliam
Two.Penny Commissiong in 1977 and Wendy Fitzwilliam in 1998.
Trinidad & Tobago has won Miss Universe twice: 1977 and 1998
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Two with Jimena Navarrete. There was a 19 year difference between both.
Puerto Rico has won Miss Universe 5 times: 1970, 1985, 1993, 2001, 2006
There are three Miss America winners from Texas: 1942, 1971, 1975
Croatia has never won Miss Universe.
Miss Cayman has never won Miss Universe.
Trinidad and Tobago won Miss World once, in 1986. The winner was Giselle Laronde.
Twice; first in 1979 with Janelle Commissiong (the first black woman to win the title), and Wendy Fitzwilliam in 1998.
Colombia has won Miss Universe twice: 1958 and 2014
As of March 2015, Trinidad and Tobago won Miss World once - it was Giselle Laronde in 1986.