This article identifies the strategies of teaching the history of transition towards democracy in Chile and Spain at the level of university education. Hence, the objective of this paper is to understand the characteristics of the evolution and development of historiography on this issue through a comparison that focuses on contents, extension as well as limitations through their respective university teaching methodology. Attempting to answer these key questions will finally lead to a deep and new insight into the art of professional historiography in general and its links and connections with more basic university levels specifically. Due to the comparative approach, this article will also add to a more global understanding of general struggles that come with teaching rather current historical processes.