Background: Laparoscopic cholecystectomy has many difficulties which include port Insertion, Dissectionof the Calot’s Triangle , Grasping of the Gallbladder , Wall thickness, Adhesion and extraction of theGallbladder. Aim of the Study: To predict how difficult cholecystectomy will be from assessing the patientpreoperatively which, in turn, help in decreasing the risks on the patients and preventing post-operativecomplications. Patients and Methods: A prospective study conducted in the department of General Surgeryat Al-Ramadi Teaching Hospital for the period of nine months from 15th of May 2018 till the 15th of February2019. It included 60 patients, all of them were undergone laparoscopic cholecystectomy for Gallstone. Patientswith common bile duct calculus, dilated common bile duct, current attack of acute cholecystitis, those withabsolute contraindications to laparoscopic cholecystectomy, The data were collected prospectively to predictthe significance of association with patients’ characteristics. The time of operation was calculated from thefirst port site incision until the last port closure. All the intra operative events were recorded. Conversionsto open cholecystectomy were done by median or subcostal laparotomy according to the surgeon’s decisionand each patient’s condition. Results: In this study, the highest proportion of operations was categorizedas easy (58.3%), 28.3% of operations were considered difficult and 13.3% of them were very difficult. Asignificant association (P < 0.05) between operation difficulty and all of the following characteristics: Aging,obesity, history of previous biliary hospitalization, thickened bladder wall, pericholecystic collection, andlarge stones. Conclusions: The difficult laparoscopic cholecystectomy can be predicted preoperativelybased on number of factors, like: obesity, previous biliary admission, gall bladder wall thickness, ultrasoundfindings (stone size and pericholecystic fluid) and aging process, evaluating of such factors minimize thecomplications of laparoscopic cholecystectomy and conversion to the open procedure.