Simulated gambling, such as playing a virtual slot machine for points rather than money, is increasingly part of the online gaming experience for youth. This study aimed to examine (1) if youth participation in simulated gambling games is associated with participation in monetary gambling; (2) if youth participation in simulated gambling games is associated with increased risk of problematic gambling when controlling for breadth of monetary gambling (i.e., number of gambling forms); and (3) if monetary expenditure and time spent playing simulated gambling games increase the risk of problematic gambling. Two samples of Australians aged 12–17 years were recruited—826 respondents through an online panel aggregator (mean age 14.1 years) and 843 respondents through advertising (mean age 14.6 years). Aim 1 was addressed using chi-square and correlation analyses. Linear multiple regression analyses were conducted to address Aims 2 and 3. The findings in both samples supported the study’s hypotheses—that (1) youth who play simulated gambling games are more likely to participate in monetary gambling, and that (2) participation and (3) time and money expenditure on simulated gambling are positively and independently associated with risk of problematic gambling when controlling for the number of monetary gambling forms, impulsivity, age and gender. To better protect young people, simulated gambling should, at minimum, emulate the consumer protection measures required for online gambling.