Objectives: The Deakin University School of Medicine commenced in 2008 as a rurally focused medical school in south-eastern Australia. This research was designed to examine the effectiveness of the school’s adoption of small regional clinical school settings. Methods: A retrospective cohort study of the first two cohorts of students was employed to assess academic performance at each of five geographically dispersed clinical training sites, with varying student cohort sizes. The Dundee Ready Education Environment Measure (DREEM) questionnaire provided quantitative data regarding the students’ perception of their educational environment. The data were analyzed using univariate and multivariate analyses. Results: The highest examination scores, and greatest satisfaction with educational environment, were associated with the clinical school that had a small-sized group of students and was not co-located with another medical school. These differences remained after adjusting for multiple potential confounding factors. Conclusion: The smaller sites appear to have provided superior support for student learning in this new medical school. This advantage diminishes when smaller cohorts are co-located with students from other medical schools. Cohort size and co-location of medical school curricula may be important independent variables for researchers to consider when comparing the results of clinical education innovations in different settings.