Educators increasingly view the high level of engagement and experiential learning offered by games as a means to promote learning. However, as with any designed learning experience, player experiences should provide an accurate representation of content to be learned. In this study, the authors investigated the DIFFUSION SIMULATION GAME (DSG) to assess the consistency of strategies effective in the game with those implied to be effective by the diffusion of innovations theory on which the game is based. They analyzed records from 2,361 completed game sessions of the DSG and compared successful and unsuccessful strategies. They further compared successful gameplay strategies with strategies suggested by the diffusion of innovations theory. The data analysis indicated that four of the seven winning strategies were inconsistent with what the theory predicts. However, this conclusion is tentative, given limitations of temporal detail in available data. These limitations imply how data should be collected to better investigate strategies that result in successful DSG gameplay. In addition, the study provides a case in which objective methods were used to analyze patterns of gameplay and offers insight on how data should be collected to analyze patterns more effectively.