This dissertation seeks to explore the possibilities of translating classical Persian poetry with troubadour lyric as its point of contact, especially in terms of its formal challenges. The focal point of this exploration is the annotated translation of two fourteenth-century Shiraz authors: Jahân Malek-Khatun, the poet with the largest divan of pre-modern Persian poetry written by a woman, and Hafez of Shiraz, one of the most canonical authors of Persian lyric poetry, known for perfecting and expanding the themes of the ghazal. Setting out from JiriLevy s concept of illusionist translation, the dissertation moves on to an overview of Persian poetics, particularly highlighting the Persian ghazal and roba i and their semantic and formal challenges for translation. At the same time, it explores how troubadour lyric — the primordial ruins of Lusophone poetry — can provide elements that help overcome these challenges. The translation practice achieved by combining these elements is discussed through analysis of and commentary on the translations carried out.