The study analyzes a group of lesser-known icons from Wallachia, dating from the 15th century to the mid-17th century. They are Eleousa-Glykophilousa icons, sometimes mixing in a rarer iconographic detail, a phylactery with inscription held by the Infant Jesus. These icons do not descent from a single prototype, but from several related types, of Late Byzantine, Macedonian, and Cretan origins. They seemed to have entered Wallachia in two different stages. The first Eleousa icon known in Wallachia, originating in the former Metropolitan Cathedral at Curtea de Argeş and later moved to the monastery founded by Neagoe Basarab on the same spot, likely was a Late Byzantine icon from the 14th or 15th century. The Wallachian icons of the 16th century shared related iconographic characteristics. The epoch of Neagoe Basarab acted as a catalyst for the different iconographic variants of Palaiologan and post-Palaiologan tradition, both through the cult dedicated to the Mother of God that the voivode developed at the Curtea de Argeş Monastery, his emblematic aulic foundation, and through the great development and renewal of the artistic culture that he sustained in Wallachia and which was emulated later on.