Campaigns as commander
Main articles: Expedition of Amr ibn al-Asand Expedition of Abu Ubaidah ibn al Jarrah
In the year 629 Muhammad sent 'Amr ibn al-'Asto Daat al-Salaasil from where he called for reinforcements, this was known as the Expedition of Abu Ubaidah ibn al Jarrah. Muhammad sent Abu Ubaidah in command of an army that included Abu Bakr and Umar. They attacked and defeated the enemy. Later in the same year, another expedition was sent under his command to locate the routes of Qurayshi caravans. [ 5 ]
During Abu Bakr's era
When Muhammad died in 632 the matter of his successiontook place at the Saqifahof Banu Sa'ida, Abu Ubaidah was there along with Abu Bakr and Umar. Umar said to Abu Ubaidah to stretch forth his hand for the caliphate, but he refused and said to Abu Bakr to stretch forth his hand to take the pledge of alliance. After the Ridda warswhen Abu Bakr sent Khalid ibn al-Walid to Iraqto conquer it, he sent four Muslim armies into the Levant, making Abu Ubaidah commander of one of them. His target was selected to be Emessaand he was ordered to move through the Tabuk regionafter the army of Sharjeel ibn Hassana.
He remained commander in chief of the Muslim army until Khalid ibn al-Walid arrived from Iraq to Syriain 634. Abu Ubaidah was ordered by Khalid ibn al-Walid to remain where he was until Khalid ibn al-Walid reached the Ghassanidcity of Bosra, where they met. The castle surrendered the city after the Battle of Bosrain mid July 634 and 130 Muslims died in the battle.
Soon the Muslims heard of a gathering of 90,000 Byzantinearmy (Eastern Roman army) at Ajnadayn, about 15 mi (24 km) southwest of Jerusalem. All the divisions of the Muslim army, about 32,000 in number, joined Khalid at Ajnadayn on 24 July 634. Under the command of Khalid ibn al-Walid the Muslims defeated the Byzantine armythere on 30 July 634 at the Battle of Ajnadayn. After one week, Abu Ubaidah, along with Khalid, moved towards Damascus. On their way to Damascus, they defeated another Byzantine army at the Battle of Yakusain mid-August 634. Caloiis and Azrail, the governor of Damascus, led another army to stop Khalid's corps but they were also defeated in the battle of Maraj-al-Safaron 19 August 634.
The next day the Muslims reached Damascus and besieged the city, which continued for 30 days. After defeating the Byzantine reinforcements sent by Emperor Heracliusat the Battle of Sanita-al-Uqab, 20 mi (32 km) from Damascus, Khalid's forces attacked and entered the city. With Khalid's divisions investingthe city from the northeast, Thomas, the purported son-in-law of the Emperor Heraclius, surrendered the city to Ubaidah, who was besieging the Bab al-Jabiya(Jabiya Gate), on 19 September 634
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