Bilad al-Sham in the context of "Mu'awiya I"

The Umayyad Caliphate or Umayyad Empire (US: /uːˈmaɪæd/; Arabic: ٱلْخِلَافَة ٱلْأُمَوِيَّة, romanized: al-Khilāfa al-Umawiyya) was the second caliphate established after the death of the Islamic prophet Muhammad and was ruled by the Umayyad dynasty from 661 to 750. It succeeded the Rashidun Caliphate, of which the third caliph, Uthman ibn Affan, was also a member of the clan. The Umayyad family established dynastic, hereditary rule with Mu'awiya ibn Abi Sufyan, the long-time governor of Greater Syria, who became caliph after the end of the First Fitna in 661. After Mu'awiya's death in 680, conflicts over the succession resulted in the Second Fitna, and power was eventually claimed by Marwan ibn al-Hakam, from another branch of the clan. Syria remained the Umayyads' core power base thereafter, with Damascus as their capital.

The Umayyads continued the Muslim conquests, conquering Ifriqiya, Transoxiana, Sind, the Maghreb and Hispania (al-Andalus). At its greatest extent, the Umayyad Caliphate covered 11,100,000 km (4,300,000 sq mi), making it one of the largest empires in history in terms of area. The dynasty was toppled by the Abbasids in 750. Survivors of the dynasty established themselves in Córdoba which, in the form of an emirate and then a caliphate, became a world center of science, medicine, philosophy and invention during the Islamic Golden Age.

Syria (Arabic: ٱلشَّام, romanized: Ash-Shām or Shām), also known as Greater Syria or Syria-Palestine, is a historical region located east of the Mediterranean Sea in West Asia, broadly synonymous with the Levant. Throughout history, the term Syria-Palestine referred to the area between the Taurus Mountains in the north and Arabia-Sinai in the south, however in modern times the term "Syria" is used to refer solely to the Syrian Arab Republic.

The term is originally derived from Assyria, an ancient Semitic-speaking civilization centered in northern Mesopotamia, modern-day Iraq. During the Hellenistic period, the term Syria was applied to the entire Levant as Coele-Syria. Under Roman rule, the term was used to refer to the province of Syria, later divided into Syria Phoenicia and Coele Syria, and to the province of Syria Palaestina. Under the Byzantines, the provinces of Syria Prima and Syria Secunda emerged out of Coele Syria. After the Muslim conquest of the Levant, the term was superseded by the Arabic equivalent Shām, and under the Rashidun, Umayyad, Abbasid, and Fatimid caliphates, Bilad al-Sham was the name of the metropolitan province encompassing most of the region. In the 19th century, the name Syria was revived in its modern Arabic form to denote the whole of Bilad al-Sham, either as Suriyah or the modern form Suriyya, which eventually replaced the Arabic name of Bilad al-Sham.

The Muslim conquest of the Levant (Arabic: فَتْحُ الشَّام, romanized: Fatḥ al-šām; lit. 'Conquest of Syria'), or Arab conquest of Syria, was a 634–638 CE conquest of Byzantine Syria by the Rashidun Caliphate.

A part of the wider Arab–Byzantine wars, the Levant was brought under Arab Muslim rule and developed into the provincial region of Bilad al-Sham. Clashes between the Arabs and Byzantines on the southern Levantine borders of the Byzantine Empire had occurred during the lifetime of Muhammad, with the Battle of Muʿtah in 629 CE. However, the actual conquest did not begin until 634, two years after Muhammad's death. It was led by the first two Rashidun caliphs who succeeded Muhammad: Abu Bakr and Umar ibn al-Khattab. During this time, Khalid ibn al-Walid was the most important leader of the Rashidun army.

The Umayyad dynasty (Arabic: بَنُو أُمَيَّةَ, romanized: Banū Umayya, lit. 'Sons of Umayya'), or the Umayyads (Arabic: الأمويون, romanized: al-Umawiyyūn) was an Arab clan within the Quraysh tribe who were the ruling family of the Umayyad Caliphate in 661–750 and the Emirate and later Caliphate of Córdoba in 756–1031.

In the pre-Islamic period, the Umayyads were a prominent clan of the Meccan tribe of Quraysh, descended from Umayya ibn Abd Shams. Despite staunch opposition to the Islamic prophet Muhammad, the Umayyads embraced Islam before the former's death in 632. Uthman ibn Affan, an early companion of Muhammad from the Umayyad clan, was the third Rashidun caliph, ruling in 644–656, while other members held various governorships. This included Mu'awiya ibn Abi Sufyan, the long-time governor of the Levant, who opposed the fourth Rashidun caliph Ali ibn Abi Talib in the First Muslim Civil War (656–661) and afterwards founded the Umayyad Caliphate with its capital in Damascus. This marked the beginning of the Umayyad dynasty, the first hereditary dynasty in the history of Islam, and the only one to rule over the entire Islamic world of its time. Umayyad authority was challenged in the Second Muslim Civil War, during which the Sufyanid line of Mu'awiya (which includes only the three first Umayyad caliphs) was replaced in 684 by Marwan I, who founded the Marwanid line of Umayyad caliphs, which restored the dynasty's rule over the Caliphate and remained so until the fall of the Caliphate of Córdoba.

The First Fitna (Arabic: الفتنة الكبرى) was the first civil war in the Islamic community. It led to the end of the Rashidun Caliphate and the establishment of the Umayyad Caliphate. The civil war involved three main factions; the supporters of the fourth Rashidun caliph Ali, the supporters of Uthman, primarily led by Mu'awiya and Aisha, and the Kharijites.

The roots of the first civil war can be traced back to the assassination of the second caliph, Umar. Before he died from his wounds, Umar formed a six-member council which elected Uthman as the next caliph. During the final years of Uthman's caliphate, he was accused of nepotism and killed by rebels in 656. After Uthman's assassination, Ali was elected the fourth caliph. Aisha, Talha, and Zubayr opposed Ali's accession and revolted against Ali to depose him. The two parties fought the Battle of the Camel in December 656, from which Ali emerged victorious. Afterwards, Mu'awiya, the long-time governor of the Levant, refused to recognise Ali as caliph and declared war. The two parties fought the Battle of Siffin in July 657, which ended in a stalemate and arbitration.

The Second Fitna was the second civil war in the Islamic community during the early Umayyad Caliphate. It followed the death of the first Umayyad caliph Mu'awiya I in 680, and lasted for about twelve years. The war involved the defeat of three main challenges to the authority of the Umayyad dynasty, the first by Husayn ibn Ali, as well as his supporters including Sulayman ibn Surad and Mukhtar al-Thaqafi who rallied to avenge his death in Iraq, the second by Abd Allah ibn al-Zubayr who proclaimed himself caliph in Mecca and Medina and would be nominally recognized throughout most of the Caliphate, and the Kharijites who took over central Arabia and southern Iraq and Persia.

The roots of the civil war go back to the First Fitna. After the assassination of the third Rashidun caliph Uthman, the Islamic community experienced its first civil war over the immediate question of retribution for his murder. Following the assassination of the fourth Rashidun caliph Ali in 661 and the abdication of his successor Hasan the same year, Mu'awiya became the sole ruler of the caliphate. Mu'awiya's unprecedented decision to nominate his son Yazid as his heir sparked opposition, and tensions soared after Mu'awiya's death. Husayn ibn Ali was invited by the pro-Alids of Kufa to overthrow the Umayyads but was killed with his small company en route to Kufa at the Battle of Karbala in October 680. Yazid's army suppressed anti-government rebels in Medina in August 683 and subsequently besieged Mecca, where Ibn al-Zubayr had established himself in opposition to Yazid. After Yazid died in November the siege was abandoned, and Umayyad authority would soon collapse throughout the caliphate following the death of his son except in parts of Syria where Marwan I was proclaimed caliph; most provinces recognized Ibn al-Zubayr as caliph. A series of pro-Alid movements demanding to avenge Husayn's death emerged in Kufa, beginning with Ibn Surad's Penitents movement, which was crushed by the Umayyads at the Battle of Ayn al-Warda in January 685. Kufa was then taken over by Mukhtar, who rallied Husayn's supporters and the disenfranchised mawali to his cause. Though his forces routed a large Umayyad army at the Battle of Khazir in August 686, Mukhtar and his supporters were slain by the Zubayrids in April 687 following a series of battles. Under the leadership of Marwan, the Umayyads would consolidate their power over Syria and retake Egypt from the Zubayrids, and under his successor Abd al-Malik ibn Marwan, the Umayyads would reconquer Iraq after defeating the Zubayrids at the Battle of Maskin in 691 and would reassert their control over the Caliphate after killing Ibn al-Zubayr in the second siege of Mecca in 692, while their general Al-Hajjaj ibn Yusuf would suppress the Kharijites in the years afterwards.

Marwan ibn al-Hakam ibn Abi al-As ibn Umayya (Arabic: مروان بن الحكم بن أبي العاص بن أمية, romanized: Marwān ibn al-Ḥakam ibn Abī al-ʿĀṣ ibn Umayya; 623 or 626 – April/May 685), commonly known as Marwan I, was the fourth Umayyad caliph, ruling for less than a year in 684–685. He founded the Marwanid ruling house of the Umayyad dynasty, which replaced the Sufyanid house after its collapse in the Second Fitna and remained in power until 750.

During the reign of his cousin, the third Rashidun caliph Uthman (r. 644–656), Marwan took part in a military campaign against the Byzantine Exarchate of Africa (in central North Africa), where he acquired significant war spoils. He also served as Uthman's governor in Fars (southwestern Iran) before becoming the caliph's katib (secretary or scribe). He was wounded fighting the rebel siege of Uthman's house, in which the caliph was slain. In the ensuing civil war between the fourth Rashidun caliph Ali (r. 656–661) and the largely Qurayshite partisans of Aisha, Marwan sided with the latter at the Battle of the Camel. Marwan later served as governor of Medina under his distant kinsman Caliph Mu'awiya I (r. 661–680), founder of the Umayyad Caliphate. During the reign of Mu'awiya's son and successor Yazid I (r. 680–683), Marwan organized the defense of the Umayyad realm in the Hejaz (western Arabia) against the local opposition which included prominent companions as well as Muhammad’s own clan, the Bani Hashim, who revolted under the banner of Muhammad’s grandson, Husayn ibn Ali. After Yazid died in November 683, the Mecca-based rebel and sahabi Abd Allah ibn al-Zubayr declared himself caliph and expelled Marwan, who took refuge in Syria, the center of Umayyad rule. With the death of the last Sufyanid caliph Mu'awiya II in 684, Marwan, encouraged by the ex-governor of Iraq Ubayd Allah ibn Ziyad, volunteered his candidacy for the caliphate during a summit of pro-Umayyad tribes in Jabiya. The tribal nobility, led by Ibn Bahdal of the Banu Kalb, elected Marwan and together they defeated the pro-Zubayrid Qays tribes at the Battle of Marj Rahit in August of that year.

The Emirate of Córdoba, and from 929, the Caliphate of Córdoba, was an Arab Islamic state ruled by the Umayyad dynasty from 756 to 1031. Its territory comprised most of the Iberian Peninsula (known to Muslims as al-Andalus), the Balearic Islands, and parts of North Africa, with its capital in Córdoba (at the time Qurṭubah). From 756 it was ruled as an independent emirate until Abd al-Rahman III proclaimed himself as caliph in 929.

The state was founded by Abd al-Rahman I, an Umayyad prince who fled the defeat and persecution of the Umayyad clan in Bilad Al-Sham (Levant) and across the caliphate after the Abbasid revolution. The polity then flourished for the best part of three centuries, before disintegrating in the early 11th century during the Fitna of al-Andalus, a civil war between the descendants of caliph Hisham II and the successors of his hajib (court official), Almanzor. In 1031, after years of infighting, the caliphate collapsed and fractured into a number of independent Muslim taifa (kingdoms).