The explanation of underachievement and the search for its associated factors have been of constant interest in educational research. In this regard, the number of variables that have been involved in its description and explanation has increased over the years, as has the number of studies at an international level on this topic. Although much research has focused on identifying the personal, family, and school aspects that exert the greatest influence on students’ low academic performance, the literature shows the need to study the differential effects of said variables according to the countries in which the studies are conducted. The objective of this article is therefore to analyse cross-national differences in the effect of personal, family, and school characteristics on students’ academic underachievement based on data derived from the Programme for International Student Assessment (PISA) 2018. Furthermore, it aims to identify the profile that characterises students with the lowest academic performance and to estimate the importance of the selected variables in explaining low achievement across countries. To reach these goals, the multivariate technique of decision trees through the binary CART (Classification and Regression Trees) algorithm was used, allowing the estimation of both a global model and nine specific models for each of the selected countries. The results show that, despite slight differences between the countries analysed, the variables that define the general profile of students with the lowest achievement and which have shown the strongest predictive capacity for low performance are mainly linked to the students themselves. These variables are followed in importance by family aspects, which present great differences between the territories that compose the sample. Finally, teacher and school variables have shown to have a low explanatory capacity in this study. It can therefore be concluded that, although personal characteristics continue to be those that best explain academic performance, a series of contextual variables, especially related to families, appear to influence academic achievement differentially and may even hide or cancel out certain personal characteristics.