Following the pioneering studies of Umberto Gnoli at the beginning of the twentieth century, scholarship has paid little attention to the Lombard painter Giacomo da Milano, responsible in 1524 for the 'Martyrdom of Saint Sebastian', formerly in San Domenico and now in the Pinacoteca of Palazzo Vitelli alla Cannoniera in Cittą di Castello. Several documents also attest to his activity in Umbria during the first half of the sixteenth century. This study examines the painter's figurative culture and more clearly defines his catalogue of works, thanks to a number of new additions, including two tondos depicting 'David' and 'Solomon'. These are here identified as the prophets commissioned from the master by the nuns of Santa Maria di Monteluce in Perugia, intended to adorn the capsa of the 'Coronation of the Virgin', the altarpiece of the church's main altar. The latter work had been commissioned from Raphael on 12 December 1505, but, after delays and unfulfilled obligations, it was only delivered in the summer of 1525 by Giulio Romano and Giovan Francesco Penni.