The Battle of Cynoscephalae was an encounter during the Second Macadonian War fought in Thessaly in 197 BC between the Roman army, led by Titus Quinctius Flamininus, and the Antigonid dynasty of Macedon, led by Philip V.

Flamininus marched towards Pherae in search of Philip, who was at Larisa. When Flamininus began his march to Larisa he had about 32,500 to 33,400 soldiers. Besides the usual Roman troops and auxiliary units that would appear in any Roman army Flamininus's forces also included soldiers from the allied Aetolian League, light infantry from Athamania, mercenary archers from Crete, and elephants and Numidian cavalry from King Masinissa of Numidia. Philip had about 16,000 heavy infantry in phalanx formation, 2,000 peltasts, 5,500 light infantry from Illyria, Thrace, and Crete, and 2,000 cavalry for 25,500 troops overall. The two armies met , and Philip's troops were defeated in a cavalry skirmish on the hills outside the city. Both sides then marched toward Scotusa in search of food, but out of sight of each other because of the hills.

At the battle next day, Philip's right wing was on higher ground than the Roman left, and was at first successful against them. However his left wing and center- made up of another 8,000 phalangites- were still disorganized and in marching formation. They hadn't even formed the phalanx when Flamininus sent his elephants charging into them, and they routed. After breaking through, one of the Roman tribunes took twenty maniples (a smaller division of the legion) and attacked the Macedonian right wing from behind. The Macedonians were unable to reposition themselves as quickly as the Roman maniples. Now surrounded by both wings of the Roman legion, they suffered heavy casualties and fled.

After a brief pursuit, Flamininus allowed Philip to escape. According to Polybius and Livy, 5,000 Macedonians had been killed.