Puerto Rico- without a doubt this country is the best when it comes to pageantry in the Caribbean. They always send candidates who are well prepared and ready to do anything to take the title. Unfortunately they have been more successful in one pageant than the other.
In total Puerto Rico captured seven(7) titles in the big4 pageants.
Placed 19 times in Miss Universe, won 5 times.
Placed 14 times in MW, won 1 time.
Won Miss International Once.
Placed 5 times in Miss Universe, won 0 times.
Placed 23 times in MW, won 3 times.
Trinidad & Tobago- Well, there are times when this country send stunners to pageants and there are times when they need a complete makeover. They still haven't failed to capture the MW or Miss Universe crown though. In total T&T won three(3) times.
Placed 8 times in Miss Universe, won 2 times.
Placed 10 times in MW, won once.
The reason why Jamaica is before T&T is because Jamaica placed 28 times in an international pageant, while T&T placed 18 times.
Dominican Republic- this country is not a well established powerhouse, but they have been successful at-least once in two of the big4 pageants. While they still have a chance in MW, I think they are going to be ignored a lot by Miss Universe, after they backed out of hosting the pageant in 2012.
Placed 7 times in Miss Universe, won once.
Placed 7 times in MW, won once.