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The present book is an attempt to provide a comprehensive description of conditional constructions in old Italian. The study is divided into four parts. In the first one corresponding to Chapter 1 – I discuss the theoretical and methodological principles underpinning my research. The focus is on the following aspects: i) the logical form of the expression if p, q; ii) the interaction between condi- tionality, hypothesis, time, tenses and mood; iii) the role played by the linguistic and pragmatic context. In the second part (Chapter 2), I illustrate the changes affecting conditionals in the transition from Latin to Italian, and I compare vulgarizations with original Latin texts. The third part (Chapters 3-8) is the core of the whole book. In Chapter 3, I propose a classification of Old Italian conditionals according to the following types: predictives, gnomics, counterfactuals, inferentials, conversationals, interrogatives, imperatives, anankastics, optatives. I also describe if sentences expressing meanings other than the condition- al one (e.g. factuality, temporality, concessivity, correlation, etc.), and discuss the semantic and syntactic features of the so-called “hypothetical comparative sentences”, introduced by the complex connective come se (‘as if’). In Chapter 4, I present an in-depth description of the several combinations of times, tenses and moods concerning conditional constructions. In Chapter 5 I dwell on aspects such as i) the syntactic placement of the protasis and apodosis in the textual chain; ii) the occurrence of the quantifier solo (‘only’); iii) the occurrence of epistemic markers (e.g. forse ‘maybe’, certamente ‘certainly’, etc.). In Chapter 6 I outline the functions of correlatives such as e ‘and’, sì ‘thus’, allora ‘then’, dunque ‘therefore’, which give conditionals their internal cohe- sion. Chapter 7 is an overview of the various connectives which can express a conditional meaning in Old Italian, such as qualora ‘whenever’, quando ‘when’, dove ‘where’, eccetto che ‘except if” (negative conditional). In Chapter 8, I extend the analysis to those syntactic structures which express a conditional relation even though they don’t have the form of a prototypical conditional construction if p, q. In the fourth part of the book (Chapter 9), I consider the use of conditionals in different text types (i.e. narrations, chronicles, scientific treatises, arguments, legal documents) to identify their communicative functions. In the conclusive remarks, I focus on the diachrony of Italian conditionals, stressing both continuity and discontinuity issues. The book ends with a small appendix containing data on starting if sentences (incipit) in Old Italian Poetry.