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634 Battle of Ajnadayn  (Aiznadin, Ajnadin) ★ ★ ★ ★ ★
Outcome: A Byzantine defeat by the Arabs in a major battle 30 July 634
War  &  Enemy: Enemy:
Arabs
War:
Arab Conquest of Syria
Battle Type:
Pitched Battle
The Battlefield Ajnadayn Location:
South of Beit Shemesh , in Jerusalem area, in present day Israel.
Modern Country:
Israel
  The Byzantines(emperor:  Heraclius) The Enemies
Commander: Theodore (Heraclius’ brother) Khalid ibn al-Walid
Forces: 60,000 to 90,000 20,000
Losses: Heavy 575
Background story: While the two most powerful states of that era, Byzantium and Persia, were encaged in a long and exhausting war against each other, serious changes were taking place in Arabia, where Prophet Mohammad had been preaching Islam and by 630, he had successfully united most of the Arabia under his authority. When the Prophet died in June 632, Abu Bakr was elected Caliph and began a war of conquest, starting from Iraq which was conquered in a series of successful campaigns against the Sassanid Persians.
Abu Bakr's confidence grew, and after Iraq, he issued a call to arms for the invasion of Syria -a Byzantine territory- in February 634. After the Muslim conquest of the city of Bosra, the Arab leaders received information that strong Byzantine forces would gather in Ajnadayn. The Arabs decided to gather their forces and move swiftly against them.
The Byzantines, at this time, still thought they were dealing with local Arab bandits, so organized their defense only with local troops. The Arabs on the other side, knew that they had to face the Byzantines and run over them, to proceed deeper into Syria.
The Battle:
Ajnadayn
The battle started with duels between the champions of the two armies. According to Muslim sources which are the only ones available for this battle, the Byzantines lost most of their commanders in these personal combats and, for this reason, they were not able to respond effectively when Khalid ordered a general attack. Finally, their resistance collapsed and their lines were broken.
Many of the Byzantines were able to make it safely off the field, turning in three directions: some fled towards Gaza, others towards Jaffa, but the largest group of fugitives headed for Jerusalem. Khalid launched his cavalry in several regiments to pursue the enemy on all three routes, and at the hands of this cavalry the Roman army suffered even more casualties than in the two days of fighting on the plain of Ajnadayn.

The Byzantine losses were heavy but certainly not 50,000 as reported by Arabian sources. The same sources gave a figure of 575 Arab warriors lost in the battle.
Noteworthy:
Aftermath: After the battle, the Arabs conquered all of Palestine and much of Syria, including Damascus. The battle was downplayed by Byzantine historians but its results were nothing but negligible.