Prilep was founded on the ruins of the ancient Macedonian city of Styberra (Ancient

Greek: ), first a town in Macedonia and later incorporated into the Roman Empire.
Styberra, though razed by the Goths in 268, remained partly inhabited. The town was first
mentioned as Prilep in 1014, as the place where Tsar Samuil allegedly had a heart attack upon
seeing thousands of his soldiers had been blinded by the Byzantines after the Battle of
Kleidion. Byzantium lost it to the Second Bulgarian Empire, but later retook it. Prilep was
acquired in 1334 by Serbian King Duan and after 1365 the town belonged to King Vukain,
co-ruler of Duan's son, Tzar Stefan Uro V. After the death of Vukain in 1371, Prilep was
ruled by his son Marko.[5] In 1395 it was incorporated into the Ottoman Empire, of which it
remained a part of until 1913, when it entered into the Kingdom of Serbia. In the late 19th and
early 20th century, Prilep was part of the Manastir Vilayet of the Ottoman Empire. It was
occupied by Bulgaria between 17 November 1915 and 25 September 1918 during World War
I. In 1918 Prilep became part of the Kingdom of Serbs, Croats and Slovenes, and from 1929
to 1941 it was part of the Vardar Banovina of the Kingdom of Yugoslavia. On 8 April 1941,
just two days after the start of the Axis invasion of Yugoslavia, Prilep was occupied by the
German Army, and on 26 April 1941 by the Bulgarian Army. Together with most of Vardar
Macedonia, Prilep was annexed by the Kingdom of Bulgaria from 1941 to 1944. On 9
September 1944 Prilep was liberated for a short time by the Yugoslav Partisans, but the
German Army soon seized control of the town again. Prilep was definitively liberated on 3
November 1944. From 1944 to 1991 the town belonged to the Socialist Federal Republic of
Yugoslavia, as part of its constituent Socialist Republic of Macedonia. Since 1991 the town
has been part of the Republic of Macedonia.