Recent areal and typological research has brought to light several syntactic features which English shares with the Celtic languages as well as some of its neighbouring western European languages, but not with (all of) its Germanic sister languages, especially German. This study focuses on one of them, viz. the so-called it-cleft construction. What makes the it-cleft construction particularly interesting from an areal and typological point of view is the fact that, although it does not belong to the defining features of so-called Standard Average European (SAE), it has a strong presence in French, which is in the ‘nucleus’ of languages forming SAE alongside Dutch, German, and (northern dialects of) Italian. In German, however, clefting has remained a marginal option, not to mention most of the eastern European languages which hardly make use of clefting at all. This division in itself prompts the question of some kind of a historical-linguistic connection between the Celtic languages (both Insular and Continental), English, and French (or, more widely, Romance languages). Before tackling that question, one has to establish whether it-clefting is part of Old (and Middle) English grammar, and if so, to what extent it is used in these periods. In the first part of this article (sections 2 and 3), I trace the emergence of it-clefts on the basis of data from The York–Toronto–Helsinki Corpus of Old English Prose and The Penn–Helsinki Parsed Corpus of Middle English, second edition. Having established the gradually increasing use of it-clefts from OE to ME, I move on to discuss the areal distribution of clefting among European languages and its typological implications (section 4). This paves the way for a discussion of the possible role played by language contacts, and especially those with the Celtic languages, in the emergence of it-clefting in English (section 5). It is argued that contacts with the Celtic languages provide the most plausible explanation for the development of this feature of English. This conclusion is supported by the chronological precedence of the cleft construction in the Celtic languages, its prominence in modern-period ‘Celtic Englishes’, and close parallels between English and the Celtic languages with respect to several other syntactic features.