Anghiari has been the scene of a bloody battle that made it stand out in the chronicles of the 15^th century. On 29^th June 1440, near the small Tuscan town the Florentine troops, led by Michelotto Attendolo and Giampaolo Orsini, fought against the Milanese troops of Niccolò Piccinino.

The village of Sansepolcro had a crucial role in the events that led to the battle of Anghiari. In 1438 the Papal States had taken possession of it, as foreseen in an agreement with Niccolò Fortebraccio da Montone who would have given it back at his death, which took place in '35. However, the village was occupied by Francesco Piccinino, son of the commander of mercenaries Niccolò Piccinino. Both, beside being relatives of Fortebraccio, were at the service of the Duke of Milan. At that point Sansepolcro was besieged by the papal army with the support of the Florentine. Niccolò came to help his son and Sansepolcro was not conquered. In order to avoid the political and military ascent of Piccinino and of the Visconti of Milan that was already aiming at Umbria, a great papal and Florentine army organised and took its position near Anghiari.
On 29^th June 1440, believing it right to gain from the papal army's stop in Anghiari to feed the horses, Piccinino decided to attack them by surprise. The battle was not particularly bloody, as also the famous Niccolò Macchiavelli recalled by ironically saying that only one person died and what's more by falling from his horse. The Florentines, however, celebrated it as an important victory, decisive to prevent the duke of Milan from conquering the lower Tuscany.
Numerically superior and stronger with 2000 Tuscan young men that had spontaneously joined it, the Milanese army headed for Anghiari with the intention of fighting the Florentines in the early afternoon. The surprise effect was however spoiled by the massive proportion of Piccinino's troops, that were sighted much in advance on the way going from Sansepolcro to the small fortification. The battle lasted four hours, and both arrays alternated in the control of the bridge to Anghiari.
The situation was solved by a clever manoeuvre of the Florentines that managed to control the bridge by splitting the enemy troops in two. As a matter of fact, one part of them remained on one side of the bridge and was taken prisoner. The dejection of the Milanese, who had realised that they were not able to defeat an army that knew the territory much better than them, convinced them to give up. In the end there were little losses on both sides, even if according to the chronicles a good six-hundred horses remained on the field! Piccinino was called back to Lombardia and left Tuscany almost immediately.