[2] The League's army concentrated on Anghiari, a small centre of Tuscany, and comprised: 4,000 Papal troops, under Cardinal Ludovico Trevisan; a Florentine contingent of around the same size, and a company of 300 men-at-arms (knights) from Venice, led by Micheletto Attendolo.

The numerically superior Milanese force was led by the famous condottiero Niccolò Piccinino in the name of Duke Filippo Maria Visconti and reached the area on the night of 28 June.

Micheletto and the Venetians held the bridge, allowing the greater part of the League's army to form for battle, but were eventually pushed back by Milanese reinforcements led by the captains Francesco Piccinino and Astorre II Manfredi.

[3] Machiavelli, in contrast, gives a detailed account of the strategy and tactics used by both sides, but presents the battle as "a striking example of the wretched state of military discipline in those times", arguing that the mercenary knights who ran the armies of the day had no motive to fight for victory.

[4] Nor was there ever an instance of wars being carried on in an enemy's country with less injury to the assailants than at this; for in so great a defeat, and in a battle which continued four hours, only one man died, and he, not from wounds inflicted by hostile weapons, or any honorable means, but, having fallen from his horse, was trampled to death.

Hans Delbrück argues that, The great historians of the Renaissance, Machiavelli, Guicciardini, and Jovius, were agreed in stating that the condottieri waged war simply as a game and not in bloody earnest.

[3] The earliest known image, painted within a decade of the battle, is a cassone panel by an unknown artist known as the Anghiari Master, which emphasises the tournament-like nature of the conflict, with banners and ritual engagements.