Gylippus was a Spartan general during the second Peloponnesian War. He was sent to Sicily in 414B.C. to command Syracuse against the Athenians commanded by Lamachus and Nicias. His arrival restored moral and he was swift to prevent the Athenian forces from building a wall to blockade the city.

In 413B.C. he took advantage of the Athenian forces delay by blockading them in the harbour with ships. The Athenians suffered a huge defeat and Nicias was captured along with Demosthenes one of their greatest generals. Gylippus attemped to prevent the execution of these two men, however his subordinate Gongalus and the Syrcusans killed them anyway.

In 405B.C. he was Lysander's subordinate at the battle of Aegospotami. He was given the task of taking the money captured from Athens back to Sparta, from this he stole 300 talents, however when money bearing the face of an owl, which signified Athenian origin, was found in his attic Gylippus fled into exile.