Miss Cayman Islands is a national Beauty pageant, where the winner represents Cayman Islands at the international pageants like- Miss Universe and Miss World pageant. On occasion, when the winner does not qualify, in that case, the runner up is sent as a representative to the international pageant. In the year 1988-1990 the 1st Runner-up competed at Miss World pageant from Cayman Islands.

The first Miss Cayman Islands pageant was held in the year 1977, and since then, the pageant became an annual tradition that is one of the highly anticipated national events. For more than 30 years, Cayman has successfully crowned some of the most intelligent, beautiful and poised contestants who represented the country at an international level.

The Miss Cayman Islands organization believes that the pageant is one of many traditions that helps showcase the national pride of the country and ever since its establishment, has acutely advanced into a powerful organisation. The Miss Cayman pageant provides opportunities to young women to become ambassadors locally and internationally or the Cayman Islands.

2017

Miss Cayman Islands 2017 was held on 25th March 2017. The finale concluded with the crowning of Anika Conolly as the winner. Anika Conolly succeeds Miss Cayman Islands 2016 Monyque Brooks, and will now represent the country at the Miss Universe 2017 and Miss World 2017 pageant to be held later this year

2016

Monyque Brooks was crowned as Miss Cayman Islands by the outgoing titleholder, Tonie Chisholm Delgadillo in the glistening coronation gala held on January 30’ 2016 after beating 7 other crown contenders at the Lions Centre, George Town, Grand Cayman.  Erin Nicole Hislop was adjudged as the first runner up while Schilo Scott was titled as the second runner up at the same event.

2015

Miss Cayman Islands 2015 was conducted after a gap of 4 years. Last the pageant was held in the year 2011, where 1987 born Lindsay Japal was crowned as the winner. Lindsay represented Cayman Islands at Miss World and Miss Universe in the year 2012. In the year 1980 and 1982, Cayman Islands was awarded as Miss Congeniality Universe, under the representation of Dealia Walter (1980) and Maureen Theresa Lewis (1982). In 1982, Maureen Theresa Lewis, from Cayman Islands, was also placed on Top 15 in the Miss World. In 1994, Anita Lilly Bush won the title of Continental Queen of Beauty at Miss World. The Miss Cayman 2015 was Tonie Chislom, who was crowned on 31st January, 2015 at the Lions Centre.