The article examines four painted churches, almost completely unknown to scholars, dating from the sixteenth century, during which Cyprus was under Venetian rule (1473–1571). The study comprises three parts: the first examines the wall paintings of the churches and through a stylistic and iconographic investigation establishes that, albeit products of different workshops, the frescoes most likely followed similar templates; the second explores the existing affinities between those frescoes and medieval Bolognese manuscript illuminations, an association which is propounded here for the first time; the last part constitutes an effort to suggest an appropriate date for these paintings by taking into account visual evidence from Venetian Cyprus.