This is a retrospective study of 242 patients who underwent surgical orbitomy at University of California Davis Health between 1 January 2000 and 20 May 2019. The preoperative imaging with radiologist’s interpretation, clinical assessment with clinician’s interpretation of imaging, and final histopathologic diagnosis were analysed. The clinical and radiologic assessments were compared against the final histopathologic diagnosis for concordance. Individual diagnoses were grouped into related classes for analysis. Out of 242 orbitotomy procedures, 185 met inclusion criteria of documented clinical as well as final histopathologic diagnosis. The overall concordance rate between clinicians and the final histopathologic diagnosis was 75.7% (140/180) compared to a rate of 52.4% (97/185) for the radiologists’ impression. In 49.2% (91/185) of cases the final histopathology correlated with both the clinical impression and radiology report. The clinician’s highest agreement was found to be with secondary malignancies, whereas the radiologist was most correct with assessing foreign body / calcifications.