Location
Thessally, Greece
Commanders
Roman - Titus Quinctius Flamininus
Macedonian - Philip V of Macedon
Combatants
Roman - 32,000-33,000 (in addition to Roman troops, there were also allies from the Aetolian League and Numidia and Cretan Mercenaries)
Macedonian - Around 25,000 (including troops from Thrace and Crete)
Background
The Battle of Cynoscephalae (literally, the Dogs Heads), was a battle that took place during the Second Macedonian War of 200-197 BC. The war pitted the Roman Republic, triumphant from its victory in the Second Punic War, against the Kingdom of Macedonia, the land of Alexander the Great, now ruled by Philip V. The war was sparked by Philip's efforts to assert Macedonian dominance in Greece, which eventually led to the involvement of Rome.
Initially, the Roman campaign was sluggish, and neither side was able to take the upper hand. However, that changed with the arrival of new Consul Titus Quinctius Flamininus in Greece in 198 BC. Flamininus immediately went after Philip, and, after some days of near misses in the poor weather, the two sides met at Cynoscephalae.
The Battle
On the morning the the battle, the field was covered in a thick fog which made reconaissance difficult. Philip decided to send a force to take the hills on the battlefield. However, these were met by light forces and cavalry sent out by Flamininus to perform the same task. The fighting on the hills was fierce, and Flamininus thus sent in around 2,000 infantry (mainly Aetolians) to reinforce his troops on the hill.
Philip was forced to send in his horse, who were succesful in pushing the Romans down the slope of the hill. Although initially wary of sending in infantry onto the broken ground of the hills, he was emboldened by news that the Roman force was retreating, and thus sent in 8,000 infantry. Meanwhile, Flamininus' forces had, under his direction, regrouped, and were now advancing up the slopes towards Philip's phalanx, which had formed up on the crest of the hill. Flamininus personally led his left flank, mainly composed of Roman infantry, up the hill, straight into the path of the Macedonian phalanx, which proved succesful in driving them back.
However, Flamininus switched to commanding his right flank, kept in reserve, and drove a group of war elephants (loaned to him by King Masinissa of Numidia) into the Macedonian left flank, which was still in marching order, and drove it from the field. Then, showing the flexibility of the manipular system, one Roman Tribune peeled a set of maniples away from the Roman right flank, and sent them charging in behind the Macedonian right wing. The inflexible Phalanx was now surrounded on both sides, and suffered terrible casualties, eventually causing it to break and run. The Romans gave a brief chase, but allowed Philip to escape. The most reliable casualty estimates, from Livy, suggest that up to 5,000 Macedonians lost their lives, and 2,000 Romans.
The Aftermath
The defeat at Cynoscephalae smashed the power of the Macedonian kingdom. The peace that was agreed in the same year saw the other Greek states, previously vassals of the Macedonian King, freed, whilst Macedon itself was forced to disband a large proportion of its formidable army and navy. Macedon would limp on for another 30 years, before the beginning of the final Macedonian War in 171 BC, one which brought an end to the Antigonid line, and the Kingdom of Macedon itself.