The Battle of Chaeronea (338 BC), fought near Chaeronea, in Boeotia, was the greatest victory of Philip II of Macedon. There, thanks in part to the fearless cavalry charge of Philip's son and heir, Alexander, Philip (with 32,000 men) defeated the much larger (50,000 men) combined forces of Athens and Thebes, securing Macedonian hegemony in Greece and ending Athenian democracy for good.

The battle itself pitted the classical Greek phalanx of the Athenian and Theban confederates and the Macedonian phalanx of Philip. The confederate battle line formed with the Athenians holding the left wing and the Thebans holding the right wing (with the all-important extreme right flank protected by the Sacred Band). Allied Greeks occupied the center of the line. In the Macedonian line, Philip commanded the right wing. Alexander commanded the left wing and the Companion Cavalry which was situated to the rear of the Macedonian line.

As the two sides engaged, the Macedonian left held against the charge of the Thebans. Meanwhile, the Macedonian right began an organized retreat. The relatively undisciplined Athenians rushed after them, causing a break to form in the center of the confederate line. Alexander drove the cavalry (some 2,000 horse) into the gap, outflanking the Theban left. After Alexander had exploited the break in the line, the Macedonian right reversed course and advanced on the Athenians. The Athenians were subsequently routed leaving the Thebans to fight for themselves. The combinded hammer and anvil of the Macedonian cavalry and the Macedonian phalanx's left wing crushed the Thebans. The famed Sacred Band of Thebes fought to the last man in the defeat.

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• Battle of Chaeronea