In this study, we focus on early gambling practices in online games via surveys administered among primary school children and their parents. The convergence of gambling and digital games comes along with new challenges for parental awareness and mediation. The lack of an obligatory strict classification system and labelling of simulated gambling games and their gambling characteristics makes it hard for parents to identify potential risks. In addition, the online context of simulated gambling games lowers the threshold for children to be exposed to gambling activities at a very early age. Our research questions are twofold: (1) What are parents’ perspectives on children’s engagement in gambling games? (2) What do children report about their game play incorporating gambling elements? Our study therefore measures parental mediation of games of chance and explores its relation with early online gambling behaviour in children.