This exploratory paper utilises a comparative research approach to shed light upon the developmental trajectories of the Greek and Cypriot guaranteed minimum income (GMI) schemes. Our analysis indicates that, despite similarities (e.g. in the emergence of the two schemes, as part of the extensive reforms imposed during the financial crisis on the Greek and Cypriot welfare systems), there are also significant differences. These mainly relate to implementation and, ultimately, the “success” of the two schemes in attaining their declared goals. Moreover, we argue that the developmental paths followed by the Greek and Cypriot GMI schemes should be interpreted in the light of key variables (“functionalist,” “political” and “institutional”), often used to explain the establishment and further evolution of such schemes. Within this context, the relatively “superior” performance of the Cypriot GMI, compared with the Greek scheme, is largely attributed to factors such as government effectiveness and political stability.