The term 'Annual Award' can be broken down into two crossword solutions: OBIE (4 letters) and RAISE (5 letters). OBIE stands for the Off-Broadway Theater Awards, which are presented annually to recognize excellence in Off-Broadway theater. The awards are presented by the American Theatre Wing and The Village Voice. RAISE stands for the Regional Alliance for Information and Educational Services, which is an annual award given to recognize excellence in regional educational services. The award is presented by the National Association of State Boards of Education.