This chapter investigates the performance practice of the concerto delle dame in the 1580s, through close reading of three commemorative volumes: Modena MS F 1358, Lodovico Agostini’s Il nuovo Echo (1583), and Giaches de Wert’s Ottavo libro de madrigali a cinque voci (1586). It considers the discrepancy between the printed five-voice madrigals written specifically for the concerto, and the documentary record of their performance practice, accompanied by instruments and most often without lower male voices. Using the evidence, the chapter proposes solutions for adapting the repertoire to the ensemble’s performance, and shows how traces of their performance practice emerges from the printed music. Through performance investigation, the development of courtly song into dramatic song is revealed. A model for the dramatic representations of both amorous dialogue and the solo female lament is proposed, demonstrated in two works by Giaches de Wert, “Tirsi morir volea” and “Qual musico gentil.” These works, which exist in the context of wedding celebrations for Vincenzo Gonzaga, Duchess Margherita’s brother, show continuity from celebrations for Este weddings in previous decades.