Duke of Medina Sidonia  Duke of Medina Sidonia () is a peerage grandee title of Spain in Medina-Sidonia, holding the oldest extant dukedom in the kingdom, first awarded by King John II of Castile in 1380. They were once the most prominent magnate family of the Andalusian region, the best-known of whom, Don Alonso de Guzmán El Bueno, 7th Duke of Medina Sidonia, commanded the Spanish Armada at the end of the 16th century. The defeat at the hands of weather and the English in 1588 brought disgrace to this family. The House of Medina Sidonia traces its descent from Alonso Pérez de Guzmán.