The theme of transition to work of higher education graduates has been the object of growing social concern in the recent past. Within higher education institutions in Portugal – universities and non-universities – several studies started to be developed since the 90s in order to assess the trajectories of graduates into the labour market. The paper draws on data from a comparative analysis of studies conducted by the initiative of the rectory of the higher education institutions since the year 2000. This analysis is guided by two inter-related objectives: (1) to characterize similarities and differences within the trajectories of transition to work of graduates from various institutions, (2) to discuss some methodological issues especially the questions concerning what indicators to use when studying transitions. Whenever possible we will compare the Portuguese case with the situation in other European countries.  Finally, we consider that the comparative analysis will also allow us to clarify and raise questions about the theoretical and conceptual frameworks that support the studies conducted by different institutions.