During the Persian invasion of Greece by Xerxes I, Thespiai earned a lot of good press by being the only city of Boeotia to side with the Greeks. They even sent a force of 700 who stood by the Spartans until the very end. In retribution, Xerxes destroyed the city.
Throughout much of its history, Thespiai held a huge grudge against the biggest player in Boeotia, Thebes. Except in situations where Thebes controlled Thespiai, they were opposite them in pretty much every war. They sided with the Spartans during their war with Thebes (which turned out disastrous for the Spartans at the Battle of Nemea) and they eagerly lined up with Alexander the Great’s forces that marched on Thebes. I’m sure they were heartbroken when he annihilated the city.
Perhaps the most famous and richest prostitute who ever lived, Phryne, was born in Thespiai. She made her living in Athens and once bared her breasts at a trial. The statue Aphrodite of Knidos, from which we only have Roman copies, was based on her. The most famous sculptors of the time, Praxiteles and Apelles, used her as a model.
When someone asked her for funds to rebuild the walls of Thebes, she famously quipped that she would do so only if the words “Destroyed by Alexander, Restored by Phryne the courtesan” were placed outside.
A number of soldiers from Thespiai accompanied Alexander the Great in Asia, per an inscription on an altar that still exists.
Approximate time when Askra in Boeotia is destroyed by Thespiai.
Approximate time when Eutresis is settled by Thespiai.
The Battle of Thermopylae. Soldiers from Sparta, Mantinea, Tegea, Orchomenos (Arkadia), Corinth, Phlious, Thespiai, Phokis, Opuntian Lokris, and other cities are overrun by the Persians at a huge cost.
Thebes helps Thespiai suppress a democratic revolution.
July
Sparta and their allies, including Sikyon and Tegea, defeat Athens and their allies at the Battle of Nemea. On Athens side are Thebes, Lokris Opuntii, and Corinth. With Sparta are Halieis, Sikyon, Epidauros, Troizen, and Hermione. Phlious remains neutral. Pellene fights on the side of Sparta against Thespiai.
Thebes with Thespiai accomplishes a remarkable victory over Sparta at the Battle of Leuktra.
Thespiai is again razed by Thebes and its citizens expelled.
Alexander the Great demolishes Thebes after a rebellion. Perdikkas is severely wounded in the battle. Orchomenos and Thespiai fight on the side of Alexander.