The purpose of the present study was to investigate whether or not there is an association between engaging in traditional forms of gambling and engaging in high-risk stock trading and, if so, to examine game play patterns of high-risk stock traders, as well as identify any socio-demographic similarities or differences between the two groups. Logistic regressions on data from two large Canadian data sets were undertaken to examine which variables best differentiate traditional gamblers from high-risk stock traders. The results indicate that high-risk stock traders have a higher frequency of gambling, engage in a larger range of gambling activities, and are more likely to be problem gamblers. Additionally, the type of gambling activities that high-risk stock traders participate in suggests that they are a sub-group of skill-based gamblers who also prefer gambling on casino table games, sports betting, dog and horse race betting, and games of skill for money over chance based games such as electronic gaming machines, bingo, and instant win tickets. High-risk stock traders, compared to traditional gamblers were more likely to be male, have a higher income, be better educated, and to be of Asian or “other” descent, not be divorced, widowed or separated, and be self-employed or employed full-time. However, unlike other skill-based gamblers, high-risk stock traders tended to be older rather than younger, and had a high income rather than a low income.