From the moment the first Roman occupation of the island ended, Rome tried hard to get Zakynthos back, appreciating not only its geographical advantages for commerce and conquests, but also its inherent wealth and the capabilities of its people.
Meanwhile, Zakynthos had been ruled by three tyrants in succession, and in 191 BC the aristocratic leroklis sold the island to the Achaians. However, Titus Flaminius, who was to become Roman consul a few years later, happened to be present at the assembly of the Achaians at which Zakynthos was to change hands. Arguing that the island had actually been given to Rome as a war prize, and making the most of his oratorial talents, Flaminius managed to win Zakynthos back for Rome.
This did not, however, please the people of Zakynthos, and they organised an insurrection. The outraged Romans promptly dispatched a naval force to teach the islanders a lesson. They burned and destroyed whatever they could, and posted a garrison on Zakynthos. Not long after the main party had left, however, the Zakynthians, with the help of the Aetolians, drove the Roman garrison off the island again. The Roman reaction was swift. They sent off their general Fulvius, who vanquished the Aetolians and reconquered Zakynthos in 150 BC. He imposed local self-government on the Zakynthians, and forbade them any alliances with outsiders.
Fulvius' strategy seems to have borne fruit, and the Roman overlords and the local population learnt to live with each other In mutual give and take. This was demonstrated when Mithridates VI, Eupator. King of Pontus and an indefatigable enemy of Rome, sent his general Archelaos to take Zakynthos. On this occasion the islanders fought stoutly at the side of the Roman soldiers, and Archelaos had finally to call off the siege of Zakynthos and sail off home in 87 BC without having achieved his purpose.
The pirate activities of the pre-Christian years brought successive invasions of the island, mainly by Cicilian corsairs. In 67 BC Rome charged Pompey (who was to become Pompey the Great) with ridding the Mediterranean of the pirate scourge, a task he accomplished successfully (before going on to utterly defeat Mithridates). In 36 BC, Zakynthos was given to Mark Antony, but after his defeat at the battle of Actium the island came into the possession of Octavian, heir of Caesar and the sole survivor of the Second Triumvirate.
At the redistribution of the Roman provinces, Zakynthos /vas made part of the province of Achaia, which included Epirus, the Peloponnese, and all the Greek islands except Crete. To begin with, the government was by pro-consuls. When later the Romans insisted that the island govern itself again independently under its own laws, Zakynthos had to pay an annual tax to Rome and provide a certain number of men for Roman legions. In those years the island developed apace both materially and culturally, and achieved such a standing that it could regularly invite famous scholars from Rome to lecture and teach.