stylistic:style_transfer, linguistic:paraphrasing, structural:summarization, stylistic:tone, information:classification
Roman period

In 64 BC, the Roman general Pompey annexed the western part of Syria. The Romans occupied Damascus and subsequently incorporated it into the league of ten cities known as the Decapolis which themselves were incorporated into the province of Syria and granted autonomy.

The city of Damascus was entirely redesigned by the Romans after Pompey conquered the region. Still today the Old Town of Damascus retains the rectangular shape of the Roman city, with its two main axes: the Decumanus Maximus (east-west; known today as the Via Recta) and the Cardo (north-south), the Decumanus being about twice as long. The Romans built a monumental gate which still survives at the eastern end of Decumanus Maximus. The gate originally had three arches: the central arch was for chariots while the side arches were for pedestrians.

In 23 BC, Herod the Great was given lands controlled by Zenodorus by Caesar Augustus and some scholars believe that Herod was also granted control of Damascus as well. The control of Damascus reverted to Syria either upon the death of Herod the Great or was part of the lands given to Herod Philip which were given to Syria with his death in 33/34 AD.

It is speculated that control of Damascus was gained by Aretas IV Philopatris of Nabatea between the death of Herod Philip in 33/34 AD and the death of Aretas in 40 AD but there is substantial evidence against Aretas controlling the city before 37 AD and many reasons why it could not have been a gift from Caligula between 37 and 40 AD. In fact, all these theories stem not from any actual evidence outside the New Testament but rather "a certain understanding of 2 Corinthians 11:32" and in reality "neither from archaeological evidence, secular-historical sources, nor New Testament texts can Nabatean sovereignty over Damascus in the first century AD be proven." Roman emperor Trajan who annexed the Nabataean Kingdom, creating the province of Arabia Petraea, had previously been in Damascus, as his father Marcus Ulpius Traianus served as governor of Syria from 73 to 74 AD, where he met the Nabatean architect and engineer, Apollodorus of Damascus, who joined him in Rome when he was a consul in 91 AD, and later built several monuments during the 2nd century AD.

Damascus became a metropolis by the beginning of the 2nd century and in 222 it was upgraded to a colonia by the Emperor Septimius Severus. During the Pax Romana, Damascus and the Roman province of Syria in general began to prosper. Damascus's importance as a caravan city was evident with the trade routes from southern Arabia, Palmyra, Petra, and the silk routes from China all converging on it. The city satisfied the Roman demands for eastern luxuries. Circa 125 AD the Roman emperor Hadrian promoted the city of Damascus to "Metropolis of Coele-Syria ".

Little remains of the architecture of the Romans, but the town planning of the old city did have a lasting effect. The Roman architects brought together the Greek and Aramaean foundations of the city and fused them into a new layout measuring approximately 1,500 by 750 m (4,920 by 2,460 ft), surrounded by a city wall. The city wall contained seven gates, but only the eastern gate, Bab Sharqi, remains from the Roman period. Roman Damascus lies mostly at depths of up to five meters (16 feet) below the modern city.

The old borough of Bab Tuma was developed at the end of the Roman/Byzantine era by the local Eastern Orthodox community. According to the Acts of the Apostles, Saint Paul and Saint Thomas both lived in that neighborhood. Roman Catholic historians also consider Bab Tuma to be the birthplace of several Popes such as John V and Gregory III. Accordingly, there was a community of Jewish Christians who converted to Christianity with the advent of Saint Paul's proselytization.

During the Byzantine–Sasanian War of 602–628, the city was besieged and captured by Shahrbaraz in 613, along with a large number of Byzantine troops as prisoners, and was in Sasanian hands until near the end of the war.