From the reading of certain Aristotle’s texts and of his commentators, it was established among the medieval authors the conviction about the certainty of Mathematics. Alessandro Piccolomini (1508-1578), in his work Commentarium de Certitudine Mathematicarum disciplinarum (1547), defies the epistemological status of Mathematics, arguing that its demonstrations are not potissimae. His work has rekindled the controversy on the nature of demonstrations and objects of Mathematics and led to the well-known Quaestio de Certitudine Mathematicarum. Our aim is to present the syllogistic approach made by authors who were not directly involved in the Quaestio but whose positions may be inferred based on their practices and underlying assumptions.