According to legend, a city called Sybar existed at the time of the Trojan War, founded by the Messapii Italic tribe. Later it was occupied by the Iapyges and conquered by the Romans in the 3rd century BCE, receiving the new name of Lupiae.
Under the emperor Hadrian (2nd century AD) the city was moved 3 km to NE, taking the name of Licea or Litium. Lecce had a theater and an amphitheater and was connected to the Hadrian Port (the current San Cataldo). Orontius of Lecce, locally called Sant'Oronzo, is considered to have served as the city's first Christian bishop and is Lecce's patron saint.
After the fall of the Western Roman Empire, Lecce was sacked by the Ostrogoth king Totila in the Gothic Wars. It was conquered by the Byzantines in 549, and remained part of the Eastern Empire for five centuries, with brief conquests by Saracens, Lombards, Hungarians and Slavs.
After the Norman conquest in the 11th century, Lecce regained commercial importance, flourishing in the subsequent Hohenstaufen and Angevine rule. The County of Lecce was one of the largest and most importants fiefs in the Kingdom of Sicily from 1053 to 1463, when it was annexed directly to the crown. From the 15th century, Lecce was one of the most important cities of southern Italy, and, starting in 1630, it was enriched with precious Baroque monuments. To avert invasion by the Ottomans, a new line of walls and a castle were built by Charles V, (who was also Holy Roman Emperor), in the first part of the 16th century.
In 1656, a plague broke out in the city, killing a thousand inhabitants.
In 1943, fighter aircrafts based in Lecce helped support isolated Italian garrisons in the Aegean Sea, fighting Germans during World War 2. Because they were delayed by the Allies, they couldn't prevent a defeat. In 1944 and 1945, B-24 long-range bombers of the 98th Heavy Bomb Group attached to the 15th U.S. Army Air Force were based in Lecce, from where the crews flew missions over