Several studies have observed that older Romance languages had more frequent object-verb order than their modern counterparts. This article explores the idea that contrast is crucial to understand the shift to verb-object order, as part of a more encompassing notion of boundedness, which has been frequently associated with the V2 parameter. To do so, we first show that some fronting constructions involving demonstratives were available in Old and Classical Portuguese, but not in Modern Portuguese, as a consequence of the existence of a KP projection hosting contrastive items of different sorts acting as delimitators. Second, we present some changes between Old and Classical Portuguese: (i) a decrease in fronted objects with demonstratives; (ii) an increase in the frequency of null subjects; and (iii) a small decrease in the frequency of frame setters. We propose that these shifts are to be attributed to an information-structural change correlated with a syntactic change concerning the position of complementizers and verb movement in subordinate clauses. To wit, while Old Portuguese was a symmetrical relaxed C-V2 language, Classical Portuguese was an asymmetrical one, which is reflected in terms of a reduced left periphery of subordinate clauses in the latter, in which KP cannot be projected. The article presents some implications of this account for the derivation of basic word order patterns and of clitic interpolation in Old Portuguese and for the loss of V2 in the history of Portuguese. These results suggest that the connection between boundedness, contrast and V2 grammars can be profitably explored in Old Romance languages.