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2 Miss Universe winners are from Trinidad & Tobago:1977: Janelle Commissiong1998: Wendy Fitzwilliam
Two with Jimena Navarrete. There was a 19 year difference between both.
Two.Penny Commissiong in 1977 and Wendy Fitzwilliam in 1998.
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.
Colombia has won Miss Universe twice: 1958 and 2014
Miss Kentucky has won Miss America once, in 2000.
Since the founding of the Miss Texas Scholarship Foundation, there have been 77 Miss Texas winners (as of November 2014). Of those, 3 have gone on to win Miss America.
Colombia has won Miss Universe 2 times: 1958 and 2014
There are many previous Miss America winners. The last five winners were Mallory Hagan, Laura Kaeppeler, Teresa Scanlan, Caressa Cameron, and Katie Stam.