The first significant date in the history of Scupi was the year 168 BC when the Romans definitely came to rule over the Macedonians. Scupi later obtained a status of colony where deserved veterans were settled, mostly veterans of the seventh legion of Claudius. The status was given in the time of the Flavius dynasty. According to the inscription with the abbreviations Coloniae Flaviae Felix Domitiana, some researchers think that it was the time of Domitian. But regarding the inscriptions from the tombstones it is known that the territory of Scupi was settled by veterans of other legions, as well: V Macedonica, III Italica, III Macedonica ala Flavia, XIII Gemina, IV Scythica. The veterans of the Roman legions came from different parts of the Roman Empire, from northern Italy, Spain, Syria, Dalmatia, Istria, Asia Minor etc. After the foundation of the Roman province Dardania, Scupi became main administrative, cultural, economical and religious center of the entire region.
According to the ancient history, Scupi was known as the most important city in the region of the Middle and Eastern Balkans, in the Roman period. After the adoption of the Edict of Milan, in the year 313 AD, it became a seat of the episcopate. The city was totally destroyed by the earthquake in 518, which was mentioned by Comes Marcellinus, a famous historian from the VI century AD. That was the time of the great Emperor
Justinian, who was born near Scupi, in Tauresium, today's village of Taor, 30 km away from Skopje. The city of Scupi had a very good location and to a large extent fulfilled the conditions for erecting an Antique city, which was at that time set by the renown architect Vitruvius.
The theatre according to a fragment of architectural decoration was one of the most beautiful buildings in the city and one of the most magnificent theatres in Ancient Macedonia. The remains of the monumental scene are visible today.
The ancient aqueduct is located on the periphery of Skopje. It was built out of stone and bricks, with massive columns over which there are exactly 55 arcs. The old aqueduct, built of brick and stone is a monument from the 6th century AD. It supplied the city of Skupi with water from Mount Skopska Crna Gora.
There are different presumptions about the time of its construction. Some people claim that it is a Roman building and others that it comes from the Byzantine period, somewhere after the 6th century when the Byzantine Emperor Justinian I, in honour of his birthplace, decided to rebuild the ancient city of Scupi, devastated by the earthquake of 518, and built the new city on the spot of present day Skopje and named it Justiniana Prima after himself.
The aqueduct was still in use during the Ottoman times when it supplied fresh water to the 70 hammams (public baths) and the 110 water fountains of Skopje. The Ottomans did some reparations on the aqueduct as some of the small arches (standing between the large ones, made to make the structure lighter) have pointed shape, typical for the eastern culture.
The aqueduct probably stopped to be in use after 1689 when the Austrian General Picolomini conquered and burned the city and Skopje lost its importance and splendor.