Seventeen paintings fall into this period. Of these, twelve are Italian; five come from The Netherlands. Fourteen of these paintings came to the University of Wisconsin prior to the founding of the Chazen Museum of Art in 1970, among which nine were donated by the Samuel H. Kress Foundation specifically with the new museum in mind. The most important painting in the entire group may well be the Adoration of the Shepherds executed by Giorgio Vasari in 1570-71, which came from the estate of a private collector in Milwaukee. The earliest is The Mourning Madonna of ca. 1375, a panel painting by Andrea Vanni. Colijn de Coter's Pietà modestly represents Flemish painting. Although visually striking, two of the panels of this triptych have been heavily restored. St. Anno Receiving the Donation of Sieberg from the altarpiece of St. Anno and St. Agilolfus (ca. 1520) is an excellent example of Antwerp mannerism. A small panel attributed to Jan Gossaert demonstrates the impact of Italian humanism on Flanders.

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