The paper explores two of the festal sermons written by Kievan Metropolitan Gregory Tsamblak (†1419/20) – one dedicated to the Nativity of the Theotokos, the other to her Dormition. The majority of Tsamblak’s liturgical sermons follow a classical model in which exegetic and the diegetic component play an equal part in the construction of the text, while some of his sermons (and in particular those with eschatological connotations) develop exegetic and epideictic components at the expense of the narrative ones. However, Tsamblak’s two Mariological sermons stand out of this classification, as the one celebrating the Nativity of the Virgin contains exegetical elements only (and no narrative), while the sermon dedicated to her Dormition presents no exegetic component. Why did Tsamblak decide to compose these two pieces in formats completely different from each other, and from the rest of his sermons? The paper tries to examine Tsamblak’s seemingly peculiar choice by contextualizing the two texts within late Byzantine Mariological written and visual tradition.