This article presents the results of a series of preliminary comparisons, between the Portuguese and Romanian cultural contexts, on the individualism-collectivism (IND/COL) cultural dimension. The IND/COL was evaluated with the Individualism-Collectivism Questionnaire – ICQ –, constructed in New Zealand by Shulruf, Hattie and Dixon (2003, Anonymous Questionnaire of Self-Attitudes –AQSA), and adapted to the Portuguese and Romanian contexts by Ciochină and Faria (2007), using studies of confirmatory factor analysis. The ICQ composed by 26 items, 15 evaluating the IND scale– with three subscales (Uniqueness, Competition and Responsibility) –, and 11 evaluating the COL scale – with two subscales (Harmony and Advice) –, was administered to 395 subjects, 200 Portuguese and 195 Romanian, 10th and 12th graders. On the whole, in the Portuguese and Romanian samples, the multivariate and univariate statistical analyses evidenced the existence of two independent variables – gender and cultural context –, with significant effects, main and of interaction, on the scales and subscales of the ICQ. The results were discussed taking into consideration the specificities of the educational systems in the two cultural contexts, which are inevitably shaped by socio-cultural factors characteristic of the two countries considered in the present study – Portugal and Romania.