Timoleon (Greek: Τιμολέων), son of Timodemus, of Corinth (c. 411–337 BC) was a Greek statesman and general.

As a brilliant general, a champion of Greece against Carthage, and a fighter against despotism, he is closely connected with the history of Sicily, especially Syracuse.

Timoleon was a member of the Corinthian oligarchy. In the mid 360s BC, Timophanes, the brother of Timoleon, took possession of the acropolis of Corinth and effectively made himself tyrant of the city. In response, Timoleon, who had earlier heroically saved his brother's life in battle, and after repeatedly pleading with him to desist, became involved in the assassination of Timophanes. Most Corinthians approved his conduct as patriotic; however, the tragic occurrence, the actual fratricide, the curses of his mother, and the indignation of some of his fellow citizens, drove him into a self-imposed early withdrawal from politics and civic life for twenty years.

Because of inner strife, the depredations and decline in Syracuse caused by the despots Dionysius I and his son who succeeded him, and because of the repeated conflicts with powerful Carthage, a group of Syracusans sent an appeal for help to Corinth, their mother city, which reached that city-state in 344 BC. Corinth agreed to help, but her chief citizens declined to accept the seemingly hopeless task of establishing a stable government in tyrannical, fractious, insecure, and turbulent Syracuse.

Timoleon, being named by an unknown voice in the Corinthian popular assembly, was chosen by a unanimous vote to undertake the mission. He set sail for Sicily with seven ships, a few of the leading citizens of Corinth, and a small force of 700 Greek mercenaries. He eluded a Carthaginian squadron by an ingenious stratagem and landed at Tauromenium (now Taormina) in 344 BC, where he met with a friendly reception. At this time Hicetas, tyrant of Leontini, was master of Syracuse, with the exception of the island of Ortygia, which was occupied by Dionysius II, still nominally ruler.

Hicetas was defeated by Timoleon at Adranum, an inland town, and driven back to Syracuse. After his initial unexpected success, Timoleon was sent reinforcements from Corinth and some north-western Greek states. Following the siege of Syracuse, Dionysius II surrendered Ortygia in 343 BC on the condition of his being granted a safe conduct to Corinth, where he ended his life as a private, well-off, citizen.

Hicetas now received help from Carthage (60,000 men), but ill-success roused mutual suspicion; the Carthaginians abandoned Hicetas, who was besieged in Leontini, and who was then compelled to surrender. Timoleon was thus master of Syracuse.

He at once began the work of restoration, beginning with the symbolic act of destroying the citadel constructed and used by the tyrants to oppress the people of Syracuse, and replacing it with a courthouse. He brought new settlers to depopulated Sicily from all over Greece, and re-established a popular government on the basis of the democratic laws of Diocles. The amphipolos, or priest of Olympian Zeus (ἀμφίπολος Διὸς Ὀλυμπίου), who was chosen annually by lot out of three clans, was invested with the chief magistracy. The impress of Timoleon's reforms seems to have lasted to the days of Augustus.