Federico was born in Castello di Petroia in Gubbio, the illegitimate son of Guidantonio da Montefeltro, lord of Urbino, Gubbio and Casteldurante, and Duke of Spoleto. Two years later he was legitimized by Pope Martin V, with the consent of Guidantonio's wife, Caterina Colonna, who was Martin's niece. In 1437 he was knighted by Emperor Sigismund, and in the same year he married Gentile Brancaleoni in Gubbio. At sixteen he began a career as condottiero under Niccolò Piccinino. On 22 July 1444, his half-brother Oddantonio da Montefeltro, recently created Duke of Urbino by Pope Eugene IV, was assassinated in a conspiracy: Federico, whose probable participation in the plot has never been established, subsequently seized the city of Urbino. However, the financial situation of the small dukedom being in disarray, he continued to wage war as a condottiero. After six years in the service of Florence, Federico was hired in 1450 by Sforza, now Duke of Milan. However, he could not perform his duties as he lost his right eye during a tournament. He subsequently carried a vast and disfiguring scar for the rest of his life, so that it was necessary to portray him only on his "good" side. Malatesta profited from his injury to obtain the position under Sforza, whereupon Federico in October 1451 accepted instead a proposal by Alfonso V of Aragon, King of Naples, to fight for him against Florence. After the loss of the eye, Federico – no stranger to conspiracies and one of the leaders that inspired Niccolò Machiavelli to write Il Principe – had surgeons remove the bridge of his nose (which had been injured in the incident). This improved his field of vision to a considerable extent, rendered him less vulnerable to assassination attempts – and, as can be seen by his successful career thereafter, restored his merits as a field commander. In 1453 the Neapolitan army was struck by malaria, and Federico himself risked losing his healthy eye. The Peace of Lodi of the following year seemed to deprive him of occasions to exhibit his ability as a military commander. In 1458 the death of both Alfonso and of his beloved illegitimate son, Buonconte, did not help to raise Federico's mood. His fortunes recovered when Pius II, a man of culture like him, became Pope and made him Gonfaloniere of the Holy Roman Church. After some notable exploits in the Kingdom of Naples, he fought in the Marche against Malatesta, soundly defeating him at the Cesano river near Senigallia (1462). The following year he captured Fano and Senigallia, taking Sigismondo Pandolfo prisoner. The Pope made him vicar of the conquered territories. In 1464 the new Pope Paul II called him to push back the Anguillara, from whom he regained much of the northern Lazio for Papal control. The following year he captured Cesena and Bertinoro in Romagna. In 1466 Francesco Sforza died, and Federico assisted his young son Galeazzo Sforza in the government of Milan, and also commanded the campaign against Bartolomeo Colleoni. In 1467 he took part in the Battle of Molinella. In 1469, on the death of Sigismondo Pandolfo, Paul sent him to occupy Rimini: however, fearing that an excessive Papal power in the area could also menace his home base of Urbino, once having entered Rimini Federico kept it for himself. After defeating the Papal forces in a great battle on 30 August 1469, he ceded it to Sigismondo's son, Roberto Malatesta. In 1482 he was called to command the army of Ercole I of Ferrara in his war against Venice, but was struck by fever and died in Ferrara in September.

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