Being one of the largest districts of Ottoman Istanbul, medīne-i Abū Ayyūb (present-day Eyüp Sultan) owned a significant status in the cityscape due to its historic core centered around the shrine complex of Abū Ayyūb al-Anṣārī (d. ca. 669), a well-known anṣār and the host of the Prophet Muhammad in Medina. As various medieval Arabic sources attest, he lost his life during the Umayyad Siege of Istanbul in the seventh century and was buried around the city walls. Claimed to be discovered following Ottoman conquest of Constantinople, his grave turned into a shrine and a principal place of ziyāra. At the crossroad of early Islamic, Byzantine and Ottoman periods, this grave signified a representational sacred space imbued with religious and political symbolism. Integrating an Islamic layer to multi-layered history of the city, its discovery pointed out divine blessing behind the conquest and symbolically purified the city. A close reading of Arabic and Turkish hagiographical narratives and chronicles reveal a multi-layered picture of the discovery with different story-lines and elements, even more than what Yerasimos argued in his Légendes d’Empire. A significant question in this regard is to what degree Ottoman sources relied on the previous Arabic narratives and produced their own version(s) and how this situation is related with presentist approaches pertaining to Islamization of the city, Ottoman legitimacy of rule, continuity and fluidity between Christian and Muslim sacred spaces. Exploring how the discovery was narrated for a variety of audiences and purposes, my paper suggests that Christian veneration of the grave and Christian intermediacy in the discovery are recurrent themes in the early Ottomans narratives, the sources of the later periods on the other hand are tended to be excluding Christian elements and agency. Instead they point out other motifs (e.g. gravestone inscribed in ʻIbrῑ (ﻋبرى) or kufic). This tendency seems to be in line with the growth of medīne-i Abū Ayyūb as a predominantly Muslim town from the sixteenth century onward at the expense of limiting non-Muslims behavior in the vicinity of the shrine. As multifarious Ottoman judicial records and imperial decrees of the sixteenth and seventeenth century demonstrate, Christians living in the vicinity of the shrine were repeatedly warned against their consumption of alcohol and the making of music. Their behaviors were found to be violating the pious atmosphere of the shrine, that functioned as a landmark between the city’s early Islamic past and Ottoman present.