The goal of this study is to investigate English and Portuguese with regard to gerundive nominalizations and derived nominals. Gerundive Nominalizations only occur in English and are regular and semantically predictable, while derived nominals are not regular and have a great range of semantic interpretations, therefore little predictability (Chomsky, 1970). In order to proceed to the contrastive study we selected two books originally written in English, from each of which a chapter was randomly taken to serve as a corpus for the analysis. Our analysis led to the following conclusions: (a) In Portuguese, the nominal infinitive is systematically used for the action gerundive structures of English; (b) for the action nominal, the Portuguese correspondence is a deverbal noun; (c) there are different verbal structures to represent factual gerundives in Portuguese; and (d) as an unexpected result, derived nominal do have semantic predictability, situation which could be considered as one of systematic polysemy.