This study examines to what extent there is a trend towards increasing labour market flexibility among Dutch school-leavers between 1992 and 2007, particularly among less educated ones. In addition, the article aims to explain this trend and increasing educational differences by economic globalization, controlled for business cycle effects. Multinomial logistic regression models are estimated using 16 cross-sections of the Dutch Labour Force Survey (1992–2007), including 16,447 labour market entrants. The results show that there is an increase in the likelihood of flexible employment between 1992 and 2007, which implies less standard employment, particularly among less educated individuals, and less unemployment, particularly among higher educated individuals. The less educated are hence doubly disadvantaged by the process of labour market flexibilization. It appears that economic globalization provides an explanation for these findings, except for the increasing educational differences in flexible employment compared to unemployment.