Physicians diagnose cholecystitis using a variety of clinical signs and imaging modalities. Diagnoses are routinely confirmed with the gold-standard histopathological examination of the excised gallbladder. This study examines the correlation between the postoperative clinical diagnosis and postoperative pathology report findings. The clinical diagnosis of acute cholecystitis had a sensitivity of 58.8%, specificity of 75.2%, positive predictive value of 53.1%, and negative predictive value of 79.2% when compared to the final pathologic diagnosis. The clinical diagnosis of chronic cholecystitis agreed with the pathologic diagnosis of chronic cholecystitis in 45 of 54 cases (83.3%) but did not agree in 8 of 54 acute cases (14.8%); a clinical diagnosis of “symptomatic cholelithiasis” was associated with pathologic diagnosis of acute cholecystitis in 85 of 388 cases (21.9%). There was a statistically significant relationship between the clinical diagnosis and final pathologic diagnosis (chi-squared > 32.91, p-value <0.001). One incidental case of malignant neoplasm was found in a patient with gallstones. Surgeons made an accurate clinical diagnosis of acute cholecystitis in one third to one half of their surgical cases; they made an accurate clinical diagnosis of chronic cholecystitis 80% of the time and correctly diagnosed neoplasms in 3 out of 4 cases. These results suggest that the mismatch between the postoperative clinical diagnosis and postoperative pathology occurs frequently enough that pathologic assessment should occur routinely after cholecystectomy.