Background: Trends in New Zealand (NZ) medical students' health and the influence of a wellbeing curricula are unknown. Methods: The author's collected self-report data from NZ medical students on 'Graduation Day' from 2014 to 2018, using a serial cross-sectional survey design with validated scales assessing psychological health, stigma, coping, and lifestyle. Comparisons were made with NZ general population same-age peers. Analyses examined trends, differences between 'cohorts' of students receiving different exposures to a wellbeing curriculum, and correlations between students' own lifestyle practices and their frequency of talking with patients about those topics. Results: Of 1,062 students, 886 participated. The authors found statistically significant self-reported increases from 2014 to 2018 for negative psychological indices, including scores for distress and burnout, suicidal thoughts in the preceding year, and the likelihood of being diagnosed with an anxiety disorder. There was a significant increase in numbers of students reporting having their own doctor as well as increased healthy coping strategies and a significant decrease in stigma scores. Academic cohorts of students who had completed a wellbeing curriculum were more likely to report high distress levels, having been diagnosed with a mood disorder, and being non-drinkers than students without wellbeing training. When compared to NZ peers, medical students smoked less, exercised more, and were less likely to have diagnosed mood and anxiety disorders, but reported more distress. The authors found a significant correlation between the amount of exercise students undertook and their likelihood to discuss exercise with patients. Conclusions: NZ medical students have better physical health than general population peers and are more likely to discuss exercise with patients if exercising themselves. However, cohorts of graduating students report increasing distress despite the implementation of a wellbeing curriculum. Research is needed into mechanisms between students' self-awareness, willingness to report distress, stigma, mind-set, coping, and psychological outcomes, to inform curriculum developers.