This study was conducted using a quantitative, non-experimental, correlation design to explore the relationships between student-patient encounters with Diabetes Mellitus and the scores on the Diabetes Mellitus OSCE during Family Medicine clerkship. The focus of the research was to explore relationships between various methods of competency measures of third-year medical students during their Family Medicine clerkship as they encountered patients diagnosed with Diabetes Mellitus (DM). A paradigm shift in medical education is taking place and driven by the Liaison Committee for Medical Education (LCME). These changes are fueled by the public outcry demanding verification of competency of our physicians. The study's focus is on the competency outcome measures from a new educational design, moving away from patient-centered education to competency-based, student-centered education and away from a norm-referenced assessment to a criterion-referenced assessment. Relevant literature on the need for competency-based medical education and various methods for implementation informed this study, including Miller (1990); Barman (2005); Barrows (1993), De Champlain, Margolis, Macmillan, and Klass (2001); Harden and Gleeson (1979); and Howley and Wilson (2004). More direct observation of student performance must be instituted with documentation of student clinical skills. Findings revealed no differences are seen in medical student competency acquisition during encounters of patients diagnosed with DM, in terms of cognitive, psychomotor, neck exam or affective measures, during the VCU SOM Family Medicine Clerkship. Significant differences are noted in the psychomotor subscale scores of the DM OSCE as the result of suburban clerkship site placement, as opposed to rural or urban sites. Finally, students at non-residencies see more patients with DM than at residency clerkship sites. Implications for further research were discussed focusing on 1) why differences were found only found in suburban clerkship sites; 2) the possibility that cultural competency understanding may play a role in these differences; 3) how do students learn about DM prior to the FM clerkship; 4) the possibility that the OSCE does not reflect community FM practice models.