Adolescence represents a significant developmental period during which experimentation with high-risk behaviors including substance use and gambling often occurs. These high-risk behaviors have been associated with multiple negative measures of social, academic and psychological functioning. Although associations have been established between alcohol use, marijuana use, mental health problems, and problem gambling in youth, research investigating possible associations between stimulant drug use and gambling is scarce. Questionnaire responses were collected from 6542 high-school students aged 12-19 years. Relationships between types and patterns of gambling with stimulant drugs [including cocaine, methamphetamine, non-medical use of stimulants, and 3,4-methylenedioxymethamphetamine (MDMA)] were examined. Chi square analyses with odds ratio calculations revealed the use of any stimulant was associated with an increased odds of gambling frequency and problem gambling among both males and females. Self-reported use of crack cocaine was associated with a higher risk of frequent gambling and use of methamphetamines was associated with a higher risk of at-risk/problem gambling. Individuals using stimulants six or more times in the past year had high likelihoods of frequent and at-risk/problem gambling behaviors. The results contribute to our understanding of stimulant drug use and its associations with gambling behaviors among high-school youth.