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.
Twice; first in 1979 with Janelle Commissiong (the first black woman to win the title), and Wendy Fitzwilliam in 1998.
Trinidad and Tobago won Miss World once, in 1986. The winner was Giselle Laronde.
Colombia has won Miss Universe twice: 1958 and 2014
Miss Kentucky has won Miss America once, in 2000.