Philip's destruction of a combined army of Athenians and Thebans on the field of Chaeronea in Boeotia, a victory gained by decisive blows of Philip's cavalry, decisively ends Greek liberty in August 338 BCE by destroying.
His real skill as a general can be seen in a maneuver of controlled retreat aimed at dislocating the advancing Greeks and creating gaps for the cavalry to strike.
Chares participates in the battle on the Athenian side, as does Demosthenes, who, according to Plutarch, flees after dropping his arms.
Whether or not Demosthenes has disgraced himself in this way, the people choose him to deliver the funeral oration over the bodies of those slain in the battle.
No accurate account survives of the course of the battle, but it ends in a total victory for Philip.
Tradition insists (probably rightly) on the valuable contribution of Alexander on the Macedonian left and suggests (perhaps wrongly) that Philip executed a feigned retreat.
The Theban Sacred Band, broken by a cavalry charge led by Alexander, simply ceases to exist.
Athens is treated mildly, its prisoners being allowed to return home without ransom.
Demades, an Athenian orator who has risen from humble origins to a leading place in politics through his vigorous speeches and shrewd ability to fathom popular opinion, had opposed Demosthenes' attempt to arouse the Athenians against Philip, but fought against the Macedonians at Chaeronea and is taken prisoner.
On his release, he helps negotiate peace between Macedonia and Athens.
