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In 1401 Giovanni I Bentivoglio took power by a coup with the support of Milan but, having turned his back on them and allied with Florence, the Milanese marched on Bologna and had him killed the following year.In 1442 Hannibal I Bentivoglio, nephew of Giovanni, recovered Bologna from the Milanese, only to be assassinated in a conspiracy plotted by pope Eugene IV three years later.

In 727-28, the city was sacked and captured by the Lombard king Liutprand, becoming part of that kingdom.Subsequently, the town began to expand rapidly (this is the period in which its famous towers were built) and it became one of the main commercial trade centres of northern Italy thanks to a system of canals that allowed barges and ships to come and go.During a campaign to support the imperial cities of Modena and Cremona against Bologna, Frederick II's son, King Enzo of Sardinia, was defeated and captured on at the Battle of Fossalta.The free commune was severely weakened by decades of infighting, allowing the Pope to impose the tyranny of his envoy cardinal Bertrand du Pouget in 1327.Du Pouget was eventually ousted by a popoular rebellion and Bologna became a signoria under Taddeo Pepoli in 1334.

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