Elevated levels of both pathological gambling (PG) and problem shopping (PS) have been reported among adolescents, and each is associated with a range of other negative health/functioning measures. However, relationships between PS and PG, particularly during adolescence, are not well understood. In this study, we explored the relationship between different levels of problem-gambling severity and health/functioning characteristics, gambling-related social experiences, gambling behaviors and motivations among adolescents with and without at-risk/problematic shopping (ARPS). Survey data from Connecticut high school students (n = 2,100) were analyzed using bivariate analyses and logistic regression modeling. Although at-risk/problematic gambling (ARPG) was not increased among adolescents with ARPS, adolescents with ARPG (vs non-gamblers) were more likely to report having experienced a growing tension or anxiety that could only be relieved by shopping and missing other obligations due to shopping. In comparison to the non-ARPS group, a smaller proportion of respondents in the ARPS group reported paid part-time employment, whereas a greater proportion of respondents reported excessive gambling by peers and feeling concerned over the gambling of a close family member. In general, similar associations between problem-gambling severity and measures of health/functioning and gambling-related behaviors and motivations were observed across ARPS and non-ARPS adolescents. However, associations were weaker among ARPS adolescents for several variables: engagement in extracurricular activities, alcohol and caffeine use and gambling for financial reasons. These findings suggest a complex relationship between problem-gambling severity and ARPS. They highlight the importance of considering co-occurring risk behaviors such as ARPS when treating adolescents with at-risk/problem gambling.