Although a number of gambling preventive initiatives have been realized with adolescents, many of them have been developed in absence of a clear and explicitly described theoretical model. The present work was aimed to analyze the adequacy of a model to explain gambling behavior referring to gambling-related cognitive distortions (Study 1), and to verify the effectiveness of a preventive intervention developed on the basis of this model (Study 2). Following dual-process theories on cognitive functioning, in Study 1 we tested a model in which mindware gap, i.e., susceptibility to the gambler's fallacy, and contaminated mindware, i.e., superstitious thinking, were the antecedents of gambling-related cognitive distortions that, in turn, affect gambling frequency and problem gambling. Participants were 306 male adolescents (M age = 17.2 years). A path analysis indicated that cognitive distortions have a mediating role in the relationship that links probabilistic reasoning fallacy and superstitious thinking with problem gambling. Following these findings, in Study 2 we developed a school-based intervention aimed to reduce gambling-related cognitive distortions acting on the above cited mindware problems. A pre-and post-test design -with a 6 months follow-up -was performed with 34 male adolescents (M age = 16.8), randomly assigned to two groups (Training and No Training), and their baseline equivalence was verified. A Mixed 2 × 2 ANOVA attested a significant Time X Group interaction, indicating a significant reduction of the cognitive distortions from pre-test to post-test only in the Training group. The follow-up attested to the stability of the training effects and the reduction of gambling frequency over time. These findings suggest that prevention strategies should address mindware problems, which can be considered as predictors of gambling-related cognitive distortions.