The aim of this contribution is to discuss three possible theoretical interpretations of grammaticalised structures in present-day Italo-Romance varieties. In particular, we discuss and analyse three diachronic case studies in relation to the generative view of grammaticalisation. The first case-study revolves around the expression of future tense and modality. This is discussed in the light of the assumption according to which grammaticalised elements result from merging elements in higher positions than their original merge positions within the lexical domain, giving rise to the upward directionality of the grammaticalisation process within the clause (Roberts, Ian G. and Anna Roussou, 2003, Syntactic change: A minimalist approach to grammaticalization. Cambridge: Cambridge University Press). The second case study challenges this view, by discussing irrealis complementisers as a case of a downward pathway of grammaticalization at the CP level. For our third case study, namely the development of (discontinuous) demonstrative structures from Latin to Romance, the rich Italo-Romance empirical evidence is analysed through the lens of a parametric account (Longobardi, Giuseppe, Cristina Guardiano, Giuseppina Silvestri, Alessio Boattini, and Andrea Ceolin, 2013, Toward a syntactic phylogeny of modern Indo-European languages, Journal of Historical Linguistics 3(1), 122-152), in order to capture the role of the relevant semantic and syntactic features within the fine-grained architecture of the DP. It will be observed that the diachronic development of some functional categories in (Italo-)Romance results from cyclic pathways of grammaticalisation, as the same category might cyclically change from more synthetic to more analytic, and vice-versa. Moreover, it will also be shown how the two theoretical approaches adopted, i.e. the cartographic model (adopted in Roberts, Ian G. and Anna Roussou, 2003. Syntactic change: A minimalist approach to grammaticalization, Cambridge: Cambridge University Press), and the parametric accounts (Longobardi, Giuseppe, Cristina Guardiano, Giuseppina Silvestri, Alessio Boattini and Andrea Ceolin, 2013, Toward a syntactic phylogeny of modern Indo-European languages, Journal of Historical Linguistics 3(1), 122-152), are able to provide a principled explanation of the structural correlates of grammaticalisation at the sentential, clausal and nominal level of investigation.