When a cavalryman at Yarmuk advanced through the ranks of the Byzantine army to challenge Khālid b. al-Walīd’s soldiers to a duel, the Muslim general turned to his men for a volunteer. The first to step forward was the companion, Maysara b. Masrūq al-ʿAbsī. Khālid b. al-Walīd, however, rejected his offer telling him: “You are an old man, and this Byzantine is a young man. I do not want you to go out to [duel with] him because an old man can hardly stand against a young man […].” Another champion offered his services. In this case, the Muslim soldier, ʿAmr b. Ṭufayl was sent back because, in the purported words of Khālid, “you are a young boy, and I fear that you cannot stand against him.” Following the Goldilocks principle, Khālid chose the ideal fighter to defend and represent the Muslim army, a man he deemed not too old and not too young and with the requisite experience to duel with the Byzantine soldiers. The chosen champion Qays b. Hubayra al-Muradī summarily dispatched the enemy, splitting his helmet and his head. The Byzantine fighter ignominiously fell dead between the forelegs of his horse, an omen of the Muslim victory to come. Descriptions of monomachies such as this one from al-Azdī’s Fuṭūḥ al-Shām and other such manifestations of “manly” behavior on the battlefield abound in conquest narratives. Still, they have generally been dismissed as unproductive topoi. This paper will use these elements of the conquest narratives to examine the constructions of gender identity in a martial context. I will mainly focus on how hegemonic masculinity was fashioned in relation to alternative masculinities. Specifically, the paper will contrast the portrayal of marginalized groups, such as women, enslaved men, the elderly, and youths on the battlefield, to that of the Muslim male elites to nuance and denaturalize hegemonic early Islamic masculinities. In this case study, I will mine the material in al-Azdī’s Futūḥ al-Shām, one of our earliest sources on the Islamic conquests that presents a sustained narrative of the events from the Ridda wars by Abū Bakr to the conquest of Syria.