In 1990, Santa Rosa joined the all star "La Puertorriqueña" project which included Andy Montañez; in the same year he was awarded the Billboard Lo Nuestro Award for Best Male Singer. He also participated in the play "La pareja dispareja" (The Odd Couple) alongside Luis Vigoreaux and Rafo Muñiz. In 1995, Santa Rosa traveled to Japan as Puerto Rico's Good Will Ambassador, where he sang "De cara al viento" (Facing the Wind) in Japanese. In 1996, the greatest hits album "Caballero de la Salsa, Vol 2" was released and he also participated in the First "Festival Presidente" in the Dominican Republic (a Latin music festival sponsored by local Presidente beer). In 1997, he sang with Andy Montañez in New York Citys Lincoln Center and later that year, with Olga Tañón at the Universal Studios Amphitheater in Hollywood, California.