Roman and Byzantine periods

Al-Shaykh Maskin has been identified as the ancient Roman-era site of "Neapolis." By the 4th-century, Neapolis had grown to become a city.^[4]

A church was consecrated there in 517 during Byzantine rule.^[5] In his short article in the Catholic Encyclopedia of 1911, Siméon Vailhé reported that many authorities at that time thought that Al-Shaykh Maskin might be the site of the ancient city and bishopric of Maximianopolis in Arabia,^[6] whose identification with nearby Shaqqa is today accepted.^[7][8]

Ottoman period

The Ottoman Empire annexed the region in 1516. During this period al-Shaykh Maskin was settled by local Bedouin tribesmen and benefited from the annual hajj pilgrimage to Mecca by supplying pilgrim caravans with camels for transportation.^[9] In 1596 al-Shaykh Maskin appeared in the Ottoman tax registers as Samsakin and was part of the nahiya of Bani Malik al-Asraf in the Qada Hawran. It had an entirely Muslim population consisting of 56 households and 17 bachelors. A fixed tax rate of 40% was paid on wheat, barley, summer crops, goats and/or beehives; a total of 17,250 akçe. 1/3 of the revenue went to a waqf.^[10]

In the 1850s al-Shaykh Maskin contained about 100 houses and all of its inhabitants were Muslims.^[11] The town's chief commodity during the 19th-century was grain, which it exported locally. Timber and cloth were the principal imports. Goods traffic was concentrated in the town's railway station which also served all the villages between Sheikh Maskin and the Lajat region. In the It grew considerably between 1891 and 1900.^[12] The town hosted the administrative offices of Hauran's local government in the latter half of this century.^[13] The population was "exclusively Muslim" according to John Murray.^[2]

Its sheikh ("chief") was Ahmed al-Hariri also known as Ahmed al-Turk who served as the Sheikh Mushaikh al-Hauran ("chief of chiefs of the Hauran"). His tribe claimed descent from the family of the Islamic prophet Muhammad and were thus known as sharifs. In the wake of the 1860 confrontations between the region's Druze and Christians, Sheikh Ahmed al-Turk led a force of 200 tribesmen to Daraa, rescuing the over 500 Christians in that town from an impending attack by the Druze of the Lejah who his forces successfully routed. He subsequently notified all the tribal chieftains of the area to spare the Christians living in the towns under his authority, to which all the tribes conformed.^[2]

In 1895 al-Shaykh Maskin became a refuge for the residents of some dozen villages destroyed by Druze fighters in response to an Ottoman decree ordering the conscription of Druze men into the Ottoman army. Ottoman troops mobilized at al-Shaykh Maskin in preparation of the conscription expedition against the Druze which was launched from the town on 15 October.^[14] Vital Cuinet wrote in 1896 that al-Shaykh Maskin's population of 800 included 400 Muslims and 400 Greek Orthodox,^[15] while Gottlieb Schumacher described it in 1897 as "large and prosperous".^[16]

Second Battle of Al-Shaykh Maskin

Early on 27 December, the 15th Brigade of the 5th Armoured Division of the Syrian Army launched the operation to capture Al-Shaykh Maskin, attacking its northern and eastern flanks.^[17] Over the following two days, the Russian air force conducted over 80 air-strikes on the town.^[18]

On 29 December, the Army captured the Brigade 82 military base, on the outskirts of Al-Shaykh Maskin, as well as the northern part of the town itself.^[19] Government forces then temporarily lost the base due to bad weather, but retook it again overnight.^[20] The following day, government forces continued with their attempts to take full control of Al-Shaykh Maskin^[21] and captured the eastern part of the town.^[22][21] This left them in control of half of Al-Shaykh Maskin.^[23] They reached the town's main square,^[24] as well as the Al-'Umari Mosque (north of the city center), while the rebels issued a distress call for reinforcements.^[25] The Army's advances were supported by another 15 Russian air-strikes.^[26]

Further attempts by the Army to advance were made between 2 and 4 January,^[27] as 43 more Russian air-strikes hit the town.^[28][29]