Context: The practice of medicine involves many stakeholders (or participant groups such as patients, doctors and trainees). Based on their respective goals, perceptions and understandings, and on what is being measured, these stakeholders may have dramatically different viewpoints of the same event. There are many ways to characterise what occurred in a clinical encounter; these include an oral presentation (faculty perspective), a written note (trainee perspective), and the patient's perspective. In the present study, we employed two established theories as frameworks with the purpose of assessing the extent to which different views of the same clinical encounter (a three-component, Year 2 medical student objective structured clinical examination [OSCE] station) are similar to or differ from one another. Methods: We performed univariate comparisons between the individual items on each of the three components of the OSCE: the standardised patient (SP) checklist (patient perspective); the post-encounter form (trainee perspective), and the oral presentation rating form (faculty perspective). Confirmatory factor analysis (CFA) of the three-component station was used to assess the fit of the three-factor (three-viewpoint) model. We also compared tercile performance across these three views as a form of extreme groups analysis. Results: Results from the CFA yielded a measurement model with reasonable fit. Moderate correlations between the three components of the station were observed. Individual trainee performance, as measured by tercile score, varied across components of the station. Conclusions: Our work builds on research in fields outside medicine, with results yielding small to moderate correlations between different perspectives (and measurements) of the same event (SP checklist, post-encounter form and oral presentation rating form). We believe obtaining multiple perspectives of the same encounter provides a more valid measure of a student's clinical performance.