As reported in the chronicle of Filippo Villani, on 28 July, the Florentine army under the command of Galeotto Malatesta advanced to Cascina a few miles from Pisa.

However, Manno Donati and his friend Bonifacio Lupi, Marquis of Soragna had organised the Florentine defences by the time the Pisans approached.

The two men prepared an advance guard on the main road to Pisa, in view of Abbey of San Savino: a group of armed Aretine and Florentine soldiers, flanked by 400–600 Genoese crossbowmen of Ricceri Grimaldi.

Hawkwood, though, waited till the sun turned in his favor to dazzle the enemy and the wind got up from the sea to bring the dust of battle in the face of the Florentines.

However, two problems contributed to his defeat; the distance of the road between the two armies was longer than calculated, minimizing the surprise; and the oppressive heat made kilns of his armored fighters, who were mostly of English and German origin, not used to fighting at that temperature.

The Florentines' German cavalry, led by Enrico di Monforte, slowed down the attack and punched through the lines to the rear of Pisan forces, reaching the baggage train.

Hawkwood quickly realized that the surprise attack had failed and, to minimise losses to his company, withdrew the bulk of his Englishmen up to the walls of San Savino.

In 1504 Michelangelo Buonarroti was commissioned by Pier Soderini to complete a celebrative fresco depicting the Battle of Cascina, to be placed in the Florentine Room of the Great Council (or Salone dei Cinquecento) of Palazzo Vecchio while Leonardo da Vinci was commissioned to complete another painting on the opposite wall to celebrate the equally important Florentine victory at the 1440 Battle of Anghiari.

[2] Though the original cartoon is lost, having allegedly been cut up by Michelangelo's rival Baccio Bandinelli, a number of copies exist, along with an engraving by Marcantonio Raimondi.