[7] In 229 BC, continuing the expansion of Illyrian power that Agron had begun, Teuta systematically[8] attacked Issa, the polis of Korkyra and Epidamnus.
In a naval battle off the island of Paxos the Illyrian fleet, arguably commanded by Demetrius, defeated the allied Achaeans and Aetolians.
The Romans annexed the southern conquests of Teuta and following the war, due to one of the conditions imposed by Rome, Illyrian warships south of Lissus were expressly prohibited.
[13] In 222 BC an Illyrian corps of 1600 men under the command of Demetrius fought with distinction at the Battle of Sellasia, where the Macedonians won a conclusive victory over the Spartans.
After an assault on Pylos in the western Peloponnese had failed they separated their forces, with Demetrius taking his chances in plundering the Cyclades while Scerdilaidas returned north.
On putting in at Naupactus with forty ships Scerdilaidas was encouraged by his brother-in-law Amynas, king of the Athamanes, to join the Aetolians in their planned invasion of Achaea.
With help from Cynaethan traitors, they attacked, seized and burned Cynaetha, a town in the north of Arcadia, located on the northern slope of the Aroanian Mountains.
[19] After returning to the Ardiaean Kingdom, Demetrius continued operations during the following winter, attacking and seizing Roman allied cities and communities in southern Illyria.
[20] The Romans who hitherto ignored the activities of their former ally, decided that the harbors on the coast of the Ardiaean Kingdom had now to be made secure, in view of the threat of another war with Carthage.
[22][23] In 219 BC, having decided that Dimallum was crucial to Demetrius' power in the region, the consul prepared to besiege the city but was able to take it by direct assault within seven days.
Next, the Romans moved against Demetrius on the island of Pharos, who awaited the attack with good troops, ample provisions and war materials behind strong fortifications, that of the city of Issa (modern Vis).
In 218 BC, the Illyrian forces soon surrendered while Demetrius deserted the island and fled to Macedonia, making his way to the court of Philip V of Macedon, who was now the Macedonian king following the death of Antigonus.
[28] Demetrius may have returned to the Ardeaian State and have been attacked by another Roman force, although the regime of Pinnes, now confirmed as king, was left intact.
The weak Ardaeai State soon fell prey to Macedonia while the partial destruction brought onto the scene the urban koina of the Parthini, Byllines, Amanatini and others.
Perhaps seeing a chance to recover his possessions in Illyria and exact a measure of revenge on Rome, Demetrius immediately advised the young king to make peace with the Aetolians, with whom Philip was at war, and turn his attentions westward.
In summarising the strategy needed for the situation, Polybius states that Demetrius said: For Greece is already entirely obedient to you, and will remain so: the Achaeans from genuine affection; the Aetolians from the terror which their disasters in the present war have inspired them.
Polybius gives as Philip's (and Demetrius') motives that: … he thought it a matter of the most vital importance to bring Illyria into a state of good order, with a view to the success of all his projects, and above all of his passage into Italy.
For Demetrius was so assiduous in keeping hot these hopes and projects in the king's mind, that Philip even dreamed of them in his sleep, and thought of nothing else but this Italian expedition.
[36] Arriving on the scene the day after the massacre and wanting to seize the acropolis, Philip asked his advisors whether the entrails of a sacrifice which had been made indicated that he should quit the citadel or hold it.