Chaeronea was the site of two important ancient battles. The first Battle of Chaeronea was fought in August 338 B.C. Macedonia, led by Philip II and his 18-year-old son Alexander (soon to be Alexander the Great), defeated the Greek poleis of Athens and Thebes ("Sacred Band"). When Macedonia won, they killed many Greeks and sold others into slavery, so Athens agreed to a treaty. Among the terms, Athens agreed to join Phillip's Hellenic union in exchange for the release of prisoners.
One ancient source on the Battle of Chaeronea is Diodorus Siculus 16.85.5-86.Sulla won a later Battle of Chaeronea, in 86 B.C., defeating Mithridates of Pontus.