Debates around common themes in Brazilian and Portuguese History have gained media visibility in both countries. In academic studies, research about Luso-Brazilian textbooks has also increased interest. With different intensities, there are refutations of approaches and terms previously used in historiography, such as “discovery”, “slaves”, “backwards peoples”, “civilisation”, and the “exceptionalism of Portuguese colonialism”, for instance. The textbooks reveal how these themes have persisted into the present day and pose a challenge to building shared narratives in a common History. This chapter analyses how the relations between Portugal and Brazil, countries interconnected by a shared colonial past, are addressed in Portuguese and Brazilian textbooks from the twentieth to the twenty-first centuries, a period marked by the growing specialisation of the school print market and the institutionalisation of public education. Therefore, a diachronic, qualitative and panoramic perspective was adopted, allowing us to observe, in the selected books, the following questions that directly interest us: (1) What were the moments of presence and also the absence of this shared history in Luso-Brazilian school textbooks from this period?; (2) In what ways was the colonial past approached in school textbooks?; (3) What themes relating to Luso-Brazilian relations are addressed in the books?; (4) What images are used in the books to represent this shared past? This chapter will be divided into three parts. First, the chapter discusses the state of the art of teaching Brazilian-Portuguese shared history. Next, it analyses a set of textbooks produced in these countries throughout the twentieth and twenty-first centuries, paying attention to the four issues mentioned above. In the conclusions, considering the current demands and debates on teaching history, we highlight the challenges faced and possible ways forward in the textbooks’ approach to this shared history today.