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/* Pre-18th century */
The War of the League of Cognac (1526–1530) pitted the League of Cognac (an alliance of France, England, Pope Clement VII, Venice, Florence, and elements of Milan) against the Habsburg dominions of Emperor Charles V—primarily Spain and the Holy Roman Empire.
By 1539, France's ally, Florence alone continued to resist Emperor Charles V's Imperial forces, which were lead by the prince of Orange of the Principality of Orange. A Florentine army under Francesco Ferruccio engaged the Imperials at the Battle of Gavinana in 1530, but although Orange himself was killed, the Imperials won a decisive victory, and the Florentine Republic surrendered ten days later. With this decisive Habsburg victory; not only did the entire League of Cognac suffer a loss, but France especially was humiliated.
==18th century==