The thesis deals with the question whether children of labour migrants in West Germany and the Netherlands who have been born in the receiving countries―2.gen. migrants―ended up in worse first jobs than natives with similar background characteristics. It describes immigration histories and national institutional arrangements that shape labour market entrances of 2.gen. migrants in the countries, who both have large groups of Turkish migrants, similar vocational training systems and labour market structures. In addition to school and firm-based apprenticeships, the Dutch vocational training system offers exclusively school-based vocational training. The question was whether firm- and school-based apprenticeships bridge labour market entrances in both countries. The thesis presents the theoretical mechanisms that shape labour market entrances of specific ethnic groups in a framework of ‘composition’ and ‘distribution’ factors. Based on SOEP and Dutch register data different event history analyses techniques were used to analyse timing and quality of entrances jointly and with regard to first full-/part-time, temporary, permanent and low/high occupational status jobs. Two ethnic groups could be distinguished (DE: Turkish vs. Italian/Spanish/Greek; NL: Turkish/Moroccan vs. Arubean/Surinamese/Netherlands Antillean). Disadvantages of Turkish 2.gen. migrants in Germany were due to their worse written language proficiency, while they persisted for Turkish and Moroccan 2.gen. migrants in the Netherlands. German apprenticeships significantly facilitated labour market entrances, while this did not apply to firm and school-based vocational training in the Netherlands. One main conclusion is that policy measures targeted at the human capital composition are not sufficient, but that additional measures supporting job search and hiring processes are necessary to improve school-to-work transitions of 2.gen. migrants in Germany and the Netherlands.