This article assesses whether women face the same challenges in the European Commission as men by examining the career paths to top political and administrative positions. Drawing on a unique dataset, it investigates whether and, if so, how and when, women are disadvantaged. First, we analyze the characteristics and experience of all Commissioners and Directors General (2004–2019) to delineate the career paths to the top positions in the organization. Secondly, we compare pathways to find that men outnumber women in all pathways. For Commissioners women are very significantly under-represented in one of three pathways and for Directors General in two of three pathways. We identify how women are disadvantaged and the extent to which the results support arguments in the comparativist literature on gender.