Objective: Both financial strain and socio-economic status (SES) or class have been found to be negatively associated with mental health for students. In the context of national changes to higher education funding, male students from low SES backgrounds may be at particular risk of developing untreated mental health difficulties because of the way such distress tends to manifest in men, and because of their lack of help-seeking. The first year of university study is a period of significant transition for young people, which can increase their vulnerability to psychological distress. This study aims to look at the association between financial disadvantage and psychological wellbeing in male first year undergraduate students, and to examine whether this is mediated by perceived financial strain and subsequent stress. Design: A quantitative cross-sectional design was used. Method: Data was collected from 164 male students using an online questionnaire. This contained measures of financial strain, stress, depression, anxiety and family affluence. Pearson’s correlation coefficients were calculated to examine associations between the study variables. Bootstrapping analyses was conducted to test for the indirect effects of financial strain and stress. Main Findings: Lower family affluence scores were not directly associated with increased scores for depression, anxiety or stress symptoms; however, they were indirectly associated with increased scores for depression symptoms, through increased financial strain. Greater financial strain was associated with increased scores for anxiety and depression symptoms, through increased stress. Serial mediation of family affluence scores to mental health symptoms through both financial strain and then stress was not found. Conclusions: The findings support the broader idea that perceptions of financial circumstances are related to psychological wellbeing in the male student population. The study also supports the idea that male students have a stress-vulnerability that may lead those with higher perceived financial strain to experience psychological distress.