Background: Reflection on both student and teacher perspectives is crucial for effective communication and professional relationships during education. Objectives: This observational cohort study aimed to compare students' self-assessment with teacher assessments, as well as with estimated self-assessment and estimated teacher-assessment, using the pictorial representation of illness and self-measure (PRISM) during an objective structured clinical examination (OSCE). Additionally, it sought to compare self-assessment and teacher-assessment with OSCE scores. Methods: Fourth-year dental students (n = 44) were included at the beginning of their clinical course. Three tasks were selected for the OSCE exams: Oral examination on a model (task 1), matrix placement (task 2), and endodontic radiograph evaluation (task 3). Objective structured clinical examination scores were rated by an independent rater. Students and one of three calibrated teachers used PRISM to evaluate their respective assessments independently and blinded from each other. The relationships between the different assessments were determined using the Pearson correlation coefficient. Results: For task 1, a moderate correlation was found between students' self-assessment and estimated self-assessment (r = 0.44, P < 0.01). For task 2, moderate correlations were observed between self-assessment and teacher-assessment, estimated teacher-assessment and teacher-assessment, as well as between self-assessment and estimated self-assessment (P ≤ 0.01). For task 3, moderate correlations were found between self-assessment and teacher-assessment, and between self-assessment and estimated self-assessment (P < 0.01). A moderate negative correlation between self-assessment and the OSCE score was observed only for task 2 (r = -0.41, P = 0.01). Moderate negative correlations between teacher-assessment in PRISM and the OSCE score were found for all three tasks (P < 0.01). Conclusions: Self-assessment and teacher-assessment using PRISM exhibited task-dependent correlations, while results for estimated assessments varied. PRISM may serve as a promising tool for feedback and discussion in the future, as it seems capable of highlighting different views and expectations in the teaching context. Further studies are needed to confirm these findings.