Within this paper we address the importance of historical and socio-cultural contexts in research and practice of athletes’ career development and transitions. We stress that not only sport participants, but also sport psychology researchers and consultants are infused by their historical and socio-cultural contexts. This is illustrated by evolutions of career development and transition research and practice in two different countries, Russia and Germany, where cardinal historical and social changes during the last decades illuminated the salience of the contextual factors. We use our European Perspectives on Athletic Retirement Project (e.g., Alfermann, Stambulova, & Zemaityte, 2004) to exemplify the contributions of recent cross-cultural studies to a better understanding of athletes’ career termination and adjustment to the post-career, and discuss the lessons learned from the Project. In conclusion, we propose how contemporary methodological approaches in cultural and cross-cultural psychology may help to develop more contextually sensitive career research and assistance to athletes.