This chapter examines the risk of being unemployed in times of the Great Recession from a school-to-work transition perspective in Germany and Greece. In contrast to a youth-age oriented framework we pay particular attention on graduates’ first five years on the labour market. Results confirm the protective function of education for both countries. Besides individual characteristics the chapter includes country-specific characteristics of institutions and macro-level information varying over time and country. Even if the Great Recession affected both countries to a rather different extent, both countries respond in a similar manner to economic downturns. In both countries types of employment contracts are correlated with the business cycle. However, different search channels are preferred in both countries.