In terms of number of placements and awards, Delaware is one of the least successful states at Miss Teen USA. However, Ashley Coleman broke the mold to win the Miss Teen USA crown in 1999.
Miss Delaware Teen USA 2000, Carrie Aiken, and 2001, Christie Aiken, are sisters. Miss Delaware Teen USA 1997, Cheryl Crowe, was the first and so far only Delaware teen to cross over to the Miss Delaware USA title. Miss Delaware Teen USA 2011, Amanda Debus, was the first, and so far only, Delaware teen to cross over from the Miss Delaware's Outstanding Teen title, she is also the only successful MAO/MUO crossover in Delaware.