Symptoms consistent with mental disorders such as anxiety and depression have reportedly increased both in prevalence and in severity among North American post-secondary student populations over the past several years. The present study examines undergraduate students’ self-reported symptoms consistent with two common mental disorders in a Canadian context, and sheds light on several factors hypothesized to predict students’ mental health outcomes, including perceived contextual stressors within the academic setting, attitudes towards and use of coping mechanisms, and perceived barriers to seeking treatment. The ultimate goal of this study is not only to examine the unique contribution of each set of factors on students’ mental health outcomes, but also to determine the ability of these determinants together to predict the severity of self-reported symptoms of depression and anxiety. Data for this investigation were obtained through original, self-administered questionnaires from a sample of 209 undergraduate students attending the University of Regina during the fall of 2014. For the statistical analysis, univariate, bivariate, and multivariate techniques were utilized. Consistent with past research completed among American college student populations, a substantial prevalence of self-reported symptoms consistent with both depression and anxiety was found among respondents. Students’ living arrangement was a significant predictor of the severity of self-reported symptoms consistent with depression, with students living off campus with family members reporting better mental health outcomes. As expected, all contextual stressors tested for made unique contributions to the prediction of students’ self-reported symptoms consistent with both depression and anxiety. Similarly, the use of negative coping mechanisms had a positive and statistically significant association with the severity of self-reported symptoms consistent with both disorders. In turn, fear of self-discovery as a barrier to treatment had a positive and statistically significant association only with the severity of self-reported symptoms consistent with depression, while fear of therapy had a positive and statistically significant relationship with the severity of self-reported symptoms consistent with both depression and anxiety. The implications of these findings for future research and intervention at the post-secondary level are discussed.