Purpose: To assess the accuracy of radiographic interpretation between the clinician and radiologist when compared to histopathology of orbital lesions. Methods: A retrospective chart review of patients at the University of California Davis Eye Center who underwent orbitotomy from 1/1/2000 to 5/22/2019 was performed. Charts with a preoperative imaging report, preoperative clinical assessment including the clinician's interpretation of imaging, and histopathologic diagnosis were included. The specific diagnoses were grouped into related classes of pathology for the analysis. The clinical and radiologic assessments were compared against the final histopathologic diagnosis for concordance. A concordance analysis was performed. Results: 242 patients (mean age 49 years, 53.5% female) were reviewed. Of these records 185 documented the clinician's clinical impression, the radiology report, as well as the histopathology report. The clinician's preoperative assessment had substantial agreement kappa = 0.72 (0.65,0.79) with the final histopathologic result and was correct in 75.7% (140/185) of cases whereas the radiology report was correct in 52.4% (97/185) with a moderate level of agreement kappa = 0.47 (0.39, 0.55). In 49.2% (91/185) of cases the final histopathology correlated with both the clinical impression and radiology report kappa = 0.58 (0.55, 0.61). Conclusions: The accurate interpretation of orbital imaging is a challenge and histopathologic examination remains the gold standard for diagnosis. While orbital imaging is a valuable diagnostic tool the interpretation of these studies is most accurate when conducted in the context of the patient's medical history, clinical exam, and with the physician most familiar with various orbital lesions.