Our choice was justified by the fact that between the two countries exist some features that make them interesting to study from the employment point of view. Thus, both countries are Latin and this is why we consider they are comparable, because employment means people, more precisely mentalities and attitudes to work. We considered that it is interesting to see how the labour market from the east Latin Europe has evolved, in a comparable, crucial period, with its counterpart from west Latin Europe. First of all, we would like to point out the fact that our intention is to analyse the periods which from the economic history point of view have influenced in a decisive manner the present evolution of the two countries. The Portugal labour market is a subject of real scientific interest (we would like to mention that even Michael Porter was interested by this topic). Our paper tries to emphasize the common and different features of the two labour markets, in order to facilitate an experience sharing process on this topic. To achieve the paperâ€(tm)s objectives statistical and cluster analysis have been used. This is one of the best ways to capture the influence of determinant factors on labour market performance. The degree of originality is given by the assumed objectives, namely studying some very up-to-date problems from an interconnected perspective (historical similarities, structural changes, labour market performance) and analyzing the Romanian situation compared to other EU countries, i.e. Portugal. The main impact of the paper will be on the practical level through the model outcomes and conclusions. One of the objectives is to look for solutions to the problems identified and to persuade policy makers to give them a greater importance. Our main contribution is represented by the fact that we have approached this topic from an economic and historical perspective, trying to find explanations for the present situation in the modern past of the two nations.