The Battle of Montgisard was fought between the Kingdom of Jerusalem and the Ayyubid Dynasty on 25 November 1177 at Montgisard, in the Levant between Ramla and Yibna. The 16-year-old Baldwin IV of Jerusalem, severely afflicted by leprosy, led outnumbered Christian forces against Saladin's troops in what became one of the most notable engagements of the Crusades. The Muslim Army was quickly routed and pursued for twelve miles. Saladin fled back to Cairo, reaching the city on 8 December, with only a tenth of his army. Muslim historians considered Saladin's defeat to be so severe that it was only redeemed by his victory ten years later at the battles of Cresson and Hattin and the Siege of Jerusalem in 1187. Saladin did defeat Baldwin IV in the Battle of Marj Ayyun and the Siege of Jacob’s Ford in 1179, only to be defeated by Baldwin again at the Battle of Belvoir Castle in 1182 and the Siege of Kerak in 1183.

Salah ad-Din Yusuf ibn Ayyub, commonly known as Saladin, was the founder of the Ayyubid dynasty. Hailing from a Kurdish family, he was the first sultan of both Egypt and Syria. An important figure of the Third Crusade, he spearheaded the Muslim military effort against the Crusader states in the Levant. At the height of his power, the Ayyubid realm spanned Egypt, Syria, Upper Mesopotamia, the Hejaz, Yemen, and Nubia.