University students are recognized as a high-risk population group who experience greater rates of poor health outcomes and mental ill-health. Commencing university is recognized as a major life transition, where students experience new financial, academic, environmental, and social pressures that can cause changes in their normal behaviors. This study explored trends in health-risk behaviors and psychological distress in commencing university students over four survey years. First-year undergraduate students, aged 17–24, from an Australian university were included. A secondary analysis was performed on data collected via cross-sectional surveys on four occasions (2016, 2017, 2019, 2020). Crude logistic regression models were utilized to investigate the association between meeting guidelines and survey year. Odds ratios for the pairwise comparison between each year are reported. In this analysis, 1300 (2016), 484 (2017), 456 (2019), and 571 (2020) students were included. Analyses showed two clear trends: students’ probability of being at high/very high risk of psychological distress (35–55%) and consuming breakfast daily (44–55%) consistently worsened over the four survey years. These findings suggest that the odds of psychological distress and daily breakfast consumption worsened over time, whilst the proportion of students engaging in some health-risk behaviors was high, highlighting the importance of early intervention during the transition to university.