The paper intends to increase the information and knowledge on graduates’ labour market entry and early career under post-communism. The specific purpose of the analysis is to examine gender differences with respect to two particular research questions: the length of time graduates need to enter the labour force and find a first job; the odds for becoming unemployed during the first five years spent in labour force. Data from the recent HEGESCO project (www.hegesco.org) are employed in the paper. The data collection has occurred in 2008 / 2009 and refers to those diploma holders who completed their studies five years earlier in 2002 / 2003. The project involved five nations: Hungary, Lithuania, Poland, Slovenia and Turkey. The present study deals with three former communist countries: Hungary (N=1533), Poland (N=1200) and Slovenia (N=2923). The paper provides background information on these three countries in terms of their institutional features related to the school system and the labour market. Both descriptive (bivariate) and causal (multivariate) techniques are applied in the study. The Kaplan-Meier survival analysis is used to examine gender differences in labour market entry in the three countries. For investigating the determinants of possible unemployment experience (did it occur or not), the logistic regression method is applied. In addition to gender variation, data offer a large variety of predictors and control variables informing about various characteristics of the study program (field of study, BA/MA, full-time / part-time, first degree gained) as well as about the respondent’s involvement during studies (voluntary / student organization activity, internship, work experience). It is also possible to control for social origin (parental education). Results reveal that gender difference for the length of time to find a first job is significantly present only in Slovenia. For unemployment, at observed level women are definitely disadvantaged and experienced unemployment in all three countries more frequently as compared to men. On the ground of the multivariate analysis, however, the female disadvantage to have a significantly bigger chance to become unemployed in comparison to males turns out to be present only in Poland. As taking into account the large variation in the compositional effects, the paper elaborates on how these features bring advantages or disadvantages for males and females to avoid unemployment. On this ground it is impossible to conclude about a better or worse situation regarding the rank order of the three countries.