The objective structural practical examination (OSPE) is a timed examination that assesses topographical and/or applied knowledge of anatomy with the use of cadaveric resources and medical images. This study investigated whether elements of question design (provision of clinical context, type of visual resources used, gender context, and difficulty) of an anatomy question affected students' performance and also whether there was any effect of basic demography or participation in various voluntary activities. Study participants were second-year medical students (n = 150), 83 of whom consented to fill in a questionnaire collecting demographics, revision preferences, and assessment preferences. The examination scores were matched with students' responses collected on the questionnaire and all data analyzed by multiple linear regression. Difficulty of the question was the only design element found to be significantly associated with the number of students that answered correctly (P = 0.001); clinical context, visual resources used and gender of the question were not significant. When individual students' marks were analyzed along with the questionnaire data, only the students' interest in participating in department's demonstrator program was a significant predictor of a high individual score, gender of the students showed a strong trend toward significance, with female students scoring on average higher than male students. The two part OSPE questions were dissociated and analyzed using binary logistic regression to determine whether a correct answer to Part 1 (identification of a tagged or pinned anatomical structures on a specimen or medical image) was predictive of a correct answer to Part 2 (assessment of the relevant functional, applied, or clinical knowledge), but no association was found.