Conditionals in English can traditionally be viewed according to two different perspectives. One is a simplistic approach based on certain ‘cases’; the other is centered on the truth value of the protasis and apodosis. This argument is based on the semantics of the conditional structures, regardless of the syntax involved. In a similar vein, the complexity of conditionals in Arabic stems from the fact that the syntax of the conditional structure does not necessarily point to the semantics involved. This affinity between the two language systems in terms of conditionality is examined within the context of two English translations of the Arabic religious text Sahih Muslim. The present study adopts an approach that focuses on both syntax and semantics to underline the interplay and/or dissociation of the two in practice. The study reveals that Siddiqui’s versions of translating ‘law’ (and its variant ‘law-la’) and ‘inn’ structures into English are mostly inaccurate, where the syntax-semantics interplay and/or dissociation is not duly observed in practice. Khattab’s versions, however, point to a tendency to start from the entrenched premise of literalism, which is stimulated by adopting the simplistic approach to English conditional structures, being akin to documentary translation where awkwardness is common practice.