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During the fourteenth century, the Ottoman military expansion in the Byzantine territories of Asia Minor marked a new era of broad interaction and cooperation between the two populations. Genuine efforts were made both by Ottomans and Byzantines in order to get to know each other politically, socially, and religiously. It was in this context that several theological meetings between the two sides took place. A notable example is the case of Gregory Palamas (1296-1359), the Archbishop of Thessaloniki (1347-1359). While Palamas was spending a year (1354-1355) in Ottoman captivity in Anatolia, he sent a pastoral Epistle to his flock in Thessaloniki, describing the theological discussions he was engaged in with political and religious representatives of Islam. The present thesis explores these three encounters. The thesis comprises an Introduction, five Chapters (1-5), and a Conclusion. The Introduction presents the aims of the thesis, the material examined and methodology employed, and provides a critical survey of previous research on the subject followed by a brief overview of the period which places the subject, in the historical, political, cultural, and intellectual context. Chapter 1 discusses the literary form of the three encounters in Palamas’ narrative focusing on the dialectical reasoning of Palamas and his Muslim interlocutors, i.e. rhetorical strategies, the topics of their argumentation, their ‘dialogical attitudes’. Chapter 2 examines the background, motives, and content of the first two encounters (1-2) between Gregory Palamas and political representatives of Islam, while Chapter 3 those of the third encounter (3) between Palamas and a religious Muslim functionary named Tasimanēs. Chapter 4 investigates the origin of the Ottomans’ knowledge of Christianity, the reliability of information, and the degree of their knowledge of Orthodox Christianity in this period. Chapter 5 examines the origin of Palamas’ knowledge of Islam and the way this knowledge is being used in his Epistle. The Conclusion presents the findings of the research and points to areas for further investigation. It is hoped that the present work will contribute to a better understanding of the conduct of similar interactions today, and offer an opportunity to reconsider certain stereotypes in present-day Christian-Muslim encounters.