Despite legislative statutes, international research suggests that youth engage in regulated and unregulated forms of gambling. The current study was designed as a cross-cultural, comparative analysis to assess teachers’ knowledge and attitudes regarding adolescent gambling and other high-risk behaviours. One-hundred and ninety-four teachers from two regions of Romania, with experience teaching secondary school students, completed an online survey. Results were compared to an existing study looking at the same aspects among three-hundred and ninety Canadian teachers. Results suggest that both Romanian and Canadian teachers are knowledgeable about the proportion of underage youth that participate in gambling activities. Despite this awareness, Romanian teachers perceive gambling as a more serious issue affecting youth and recognize the negative consequences of underage gambling more than Canadian teachers. This is consistent with prevention initiatives, as more Romanian than Canadian teachers believe it is the responsibility of school staff to prevent adolescent gambling and are more open to receiving prevention training in youth gambling. Although international differences were found, gambling, relative to other high-risk adolescent behaviours, remains disregarded as serious problem behaviour. These results suggest that greater strides need to be taken towards increasing international teacher training and education about the short and long-term consequences associated with adolescent problem gambling.