This chapter covers the Medieval and Renaissance periods. To provide resources for an expanded curriculum and diversified pedagogy, the chapter includes bibliographies and a discography focusing on composers of the era and relevant scholarship in areas including music making in convents, in emerging colonies, and by Black Europeans. Lesson One offers brief analytical notes on “Hor che la vaga Aurora,” a madrigal by Vittoria Aleotti. The lesson contextualizes the life and accomplishment of this woman composer through examinations of her proximity to leading poets and her connections to musical activities in convents. Her collection published by Giacomo Vincenzi situates Aleotti among the few women to have music printed before 1600. Lesson Two focuses on the Cantigas de Santa Maria, a large collection of devotional songs about the Virgin Mary produced in the Court of Alfonso X of Castile in the mid-thirteenth century. The lesson explores the Hispanic and Arabic influences on this repertoire, its role in Alfonso X’s self-representation and Reconquista politics as he pursued the long-term goal of returning the Iberian Peninsula to Christian rule, and the cultural context of recent performance practices by Medieval specialists for this music.