The aim of this work was to explore the associations between youth unemployment and youth engagement in gambling forms that have age limits, namely, slots, sports betting, and cards, both online and offline. Cross-country data were provided by the 2015 European School Survey Project on Alcohol and Other Drugs, a school survey focused on 16-year-olds. Gambling analyses included 30 countries (n = 81,229 respondents). Descriptive analysis with statistical plot diagrams was used and the computed coefficient of determination adopted to identify correlations. The suggested correlation was further tested by multilevel logistic regression analysis, controlling for gender at Level 1 and for the Inequality Human Development Index, gross domestic product/capita, and public health expenditure at Level 2. Underage gambling was associated with a higher degree of adolescent unemployment. The results indicate that youth unemployment is associated with underage gambling, implying that a broad public health framework is needed in the prevention of problem gambling.