This research relates literary analysis to philosophical speculations focused on the quest for African epistemes. The study investigates the representations of HIV/AIDS by means of two ontological entities: real-life experiences, obtained through the contributions of research participants, and literature, so as to highlight African discourses on knowledge. The empirical study was crafted through a combination of six months of ethnographic fieldwork research in Tanzania and a thorough textual analysis conducted on two selected genres of Swahili literature from Tanzania, namely drama and novels, that deal with the topic of HIV/AIDS. Firstly, I explore drama, both the playscript and the performance of Ushuhuda wa Mifupa (Ngozi 1990 - UDSM 2019), contextualized within a selection of other plays written between 1989 and 2014. Secondly, I analyse novelistic prose by looking at Mutembei’s Kisiki Kikavu (2005) and Mauya’s Firauni (2017). Finally, I focused on Mkufya’s trilogy Diwani ya Maua (Ua La Faraja 2004; Kuwa Kwa Maua 2019). The objectives of this study are to demonstrate the philosophical potential of Swahili literature, which is part of the panorama of Afrophone literatures and philosophies, and to isolate both incompatible and complementary epistemologies coexisting in Swahili literature, which are articulated through multi-genre and multi-style narrative texts.