The Battle of Cynoscephalae was fought in 197 BC between the armies of the Roman Republic and Macedon during the Second Macedonian War. In an unexpected encounter, the more flexible Roman force drew out the Macedonian phalanx and used the terrain to break it up before closing to attack from the front and from both flanks. The battle was decisive, leading to Rome's crushing victory over Philip V of Macedon.
Background[]
The end of 198 BC saw the Roman army of Titus Flaminius withdraw for the winter as King Philip V of Macedon raised a new army which included both youths and old men. By the spring of 197 BC, Philip's army stopped to forage for supplies near Pharae in the south. After Roman scouts spotted the Macedonians, Titus Flaminius and his army marched north from Boeotia, hoping to intercept Philip before he could withdraw. The two armies met at the sloping ridge of Cynoscephalae in Thessaly. The Romans had two Roman and two allied legions (20,000 legionary infantry, 2,000 velites, 2,500 equites, and 200 war elephants), plus a substantial contingent of 1,200 Epirote light infantry, 800 Cretan archers, and 6,000 infantry and 400 cavalry from the Aetolian League. Philip had 16,000 sarissa-wielding phalangists, 2,000 agema peltasts, 4,000 Illyrian and Thracian mercenaries, 1,500 Greek hoplite mercenaries, and 2,000 Thessalian and Macedonian cavalry. Each commander knew that their counterpart was close, but the fog caused disorientation among the two armies. Philip's skirmishers were sent to the ridge's summit to get a better view, but they met ten Roman cavalry squadrons and 1,000 velites, and both forces skirmished before informing their commanders of the other army's positions.
Battle[]

The initial skirmish at Cynoscephalae
Flaminius sent 2,000 Aetolian infantry and 500 cavalry to the ridge as reinforcements, and the Antigonid skirmishing force slowly withdrew to the top of the ridge and requested aid from Philip. Philip sent 3,500 cavalry and mercenary infantry to reinforce his skirmishers, and they pushed the Romans back down the slope and almost routed them completely, had it not been for the strategic skirmishing and harassment by the Aetolian allies. The sunrise led to the fog dissipating, but Flaminius' men were demoralized at the sight of their men retreating. Flaminius ordered his entire army to form up in battle order and addressed his troops at the base of the slope, professing to them that they had fought and beaten the Macedonians before. The Antigonid skirmishers then urged the King to attack while momentum was on their side, and the Macedonian army deployed in battle order. Half of Philip's troops were still foraging, so he sent his general Nicanor the Elephant to follow up when the others had returned. Philip marched the head of his phalanx up the slope, screened by his peltasts and flanked on the right by cavarly. Flaminius advanced with the left side of his line to reinforce the battle between the scouting parties, forcing the Macedonians to retreat up the slope; many were killed, while others fled back towards their King. The two armies both marched up the slope without knowing the other army's intentions, and both armies came into view of one another at the top of the hill. The phalangists charged downhill at the unprepared Romans, and the remnants of Flaminius' scouting force were unprepared and were forced back. The Antigonid and Roman cavalry clashed on the wing as the light infantry skirmished, but the main clash was in the center. The Roman left was chewed up by the bristling pike wall, and Nicanor's army began to crest the ridge on the King's left flank in a rushed marching formation.
The tide turns[]

The dead at the Battle of Cynoscephalae
Flaminius was also being pushed back towards the Roman camp, so he rode over to the Roman right and ordered them to charge at the disorganized Macedonians under Nicanor, most of whom were still arriving or not yet formed up. The phalangists, who were not deployed rigidly, were crushed, and many were killed outright or chased away by the legionaries. A Roman tribune halted 20 maniples (2,500 veteran triarii troops) on the right wing and marched his contingent across the ridge to strike the victorious phalanx of Philip from the rear as it attacked the left; the veteran legionaries then renewed their assault. This intuitive maneuver caused the inflexible phalanx to fragment, and many of its phalangists were killed. Philip was unable to gather his men, and he fled the battlefield as the Romans butchered the remaining Macedonians. A group of Macedonian phalangists raised their pikes to the sky to surrender, but the furious legionaries charged in and massacred all of them. The Romans only lost 700 dead (mostly on their brave left), while the Antigonids lost 8,000 dead and 5,000 captured.