The design of this Madonna was evidently inspired by Perugino's Pala dei Decimviri (now in the Pinacoteca Vaticana), painted for the chapel of the Palazzo dei Priori at Perugia. Although probably designed by 1485, this was not finished until 1496 although it was evidently known to Giovanni Santi at an earlier date. Pintoricchio reverses the pattern, but turns the head of the Virgin to face in the same direction as Christ and alters the position of the left hands of both the Virgin and the Child, introducing the swathe of yellow drapery pulled up to reveal the latter's stomach.
The reference to the Pala dei Decimviri was no doubt deliberate and this suggests a date of circa 1495-1502 when the artist was based at Perugia. It seems likely that the picture antedates the altarpiece of 1506 in the church of Sant'Andrea at Spello, as the Child in that panel is an elongated variation of the same prototype, his left arm now stretched across the Virgin's shoulder. The better preserved passages of this panel, the top of Christ's head and his yellow drapery, parts of the Virgin's left hand and the landscape would seem to be worthy of Pintoricchio himself. A variant, in a gold ground, in which the Child is in a tunic, originally in the Saxon royal collection was sold at Sotheby's, 23 March 1969, lot 103 (F. Todini, La Pittura Umbra, Milan, 1989, p. 290, as Pintoricchio, 'parzialmente ridipinta').