This chapter discusses how Portuguese History textbooks deal with Iberian Colonialism in the 8th and 9th grades. The reason for the study is that these two grades, when most students are 13 or 14 years old, are the last in which History is compulsory for all students in Portugal. It comprises the study of the so-called Age of Discoveries, the nineteenth and twentieth centuries’ colonialism, and African independencies in a broader sense. On the other hand, even today, with a somewhat imperial nostalgia, syllabi and textbooks discuss slavery and colonialism in a way that specific authors described as benign. Echoing the lush-tropical ideas of Gilberto Freyre, which were strong during the dictatorship of the Estado Novo [New State] (1933–1974), we could say that those teaching materials continue to promote a rather heroic view of Portuguese colonialism while emphasising the brutality of the Spanish conquest of South America. Half a century after the end of the Portuguese colonial empire, the question arises: why does this view persist? Using a primarily qualitative methodology, we will analyse syllabi and textbooks from recent decades, seeking to understand continuities and ruptures in the discourse on Portuguese and Spanish colonisation. Three themes will be emphasised: (1) the question of conquest and slavery, (2) the colonial wars, and (3) the “Other” between identity and otherness. In this sense, the analysis will encompass (a) historical figures, (b) events and historical processes, and (c) narrative, primary sources, and iconography.