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The city dates back to at least 8th century BC. Around 385 BC, a Greek colony was found by Dionysius I of Syracuse by the name of Lissos (Λισσός), as part of a strategy by Dionysius to secure Syracusan trade routes along the Adriatic. Diodorus calls it a polis. The city was separated into sectors by diateichisma (Greek: διατείχισμα, “cross-wall” and there are elements of Syracusan architecture in part of its walls. At a later time it came under Illyrian rule. In 211 BC, Philip V of Macedon captured the citadel of Akrolissos, and Lissos surrendered to him. The town was later recovered by the Illyrians. It was in Lissos that Perseus of Macedon negotiated an alliance against Rome with the Illyrian king Gentius, and it was from Lissos that Gentius organized his army against the Romans. Lissos maintained a large degree of municipal autonomy under both Macedonian and Illyrian rule, as evidenced by the coins minted there. The city was of some importance in the Roman Civil War, being taken by Marc Antony and then remaining loyal to Caesar. In Roman times, the city was part of the province of Epirus Nova, its name Latinized as Lissus.