[4] In 202 BC, the Fifth Syrian War would break out, with the Macedonians allying with the Seleucids in a pact to carve up Asia Minor.

Although Rhodes and the Kingdom of Pergamum would later gain the upper hand against Philip, with a crushing defeat of his navy at the Battle of Chios,[5] they were still concerned enough about Macedon to send envoys to Rome to try and convince them to join the war.

[4] By the start of 197 BC, Philip had lost most of his earlier conquests and had been set back to Macedonia and parts of Thessaly.

For this reason, Philip decided to instead pitch camp but did still send out half his heavy infantry to search for food.

To offset the inherent risk, Philip also sent his light infantry and half of his cavalry in order to take the Cynoscephalae Hills and locate the Roman force.

[4][7] Despite their limited numbers, these reinforcements gave the Romans the upper hand, with the Macedonians now being driven back to the peaks of the Cynoscephalae and away from level ground.

[4] Though reluctant to send his phalanx into the broken, hilly terrain, as a result of the glowing reports from his forces he ordered an assault by 8,000 phalangites and 4,000 peltasts.

Unable to wait for Nicanor to arrive, Philip sent his right phalanx into the Roman left wing, driving them down the ridge, albeit at a slow pace.

Seeing Nicanor's disorganised troops, Flamininus rode to his right wing and ordered them to attack; his elephants lead the force which included their Italian allies and 4,000 Greek infantry.

Some were simply killed where they stood, others pointed their sarissas directly upwards in a sign of surrender that the Romans either ignored or failed to understand.

[4] Phillip, along with a small number of cavalry, had pulled back to the summit for a better look at the battle, only to see the collapse of his right wing and the rout of his left.

The phalanx, though very powerful head on, was not as flexible as the Roman manipular formation and thus unable to adapt to changing conditions on the battlefield or break away from an engagement if necessary.

[4][9] This assertion has been challenged by some who point out that the Romans were only able to attain victory by taking advantage of the fact that the Macedonian left wing was not fully formed, although this is also given as evidence of the phalanx's unwieldy nature when compared to the legion.

[7][9] In any case, the result of the battle of Cynoscephalae was a fatal blow to the political aspirations of the Macedonian kingdom; Macedonia would never again be in a position to challenge Rome's geopolitical expansion.