Introduction: Nowadays laparoscopic cholecystectomy is the gold standard treatment for symptomatic gallstone disease (GSD). Prediction of “difficult laparoscopic cholecystectomy” (DLC) may decrease morbidity and mortality as well as reduce the average cost of therapy. At present, very few scoring systems are available to predict the degree of difficulty during surgery. Aim and objective: To compare the outcome of intraoperative findings with preoperating scoring to predict DLC. Materials and methods: Two-hundred and nine patients were having GSD, operated by a single experienced surgeon in 2-year duration. Various preoperative predictors and intraoperative parameters of DLC were used for scoring and categorizing the difficulties, into (0–5), (6–10), and (10–15) as early, difficult, and very difficult surgical procedures, respectively. Result: History of hospitalization for acute cholecystitis, overweight with BMI ≥27.5 kg/m², palpable gallbladder, wall thickness >4 mm, and impacted stone were the most accurate preoperative predictors of DLC in the age-group of above 50 years. Statistically, a significant association was determined by comparing preoperative evaluation with the intraoperative outcome. Conclusion: The preoperative and intraoperative scoring system can be helpful for assessment, experience, and decision-making. These scoring systems deserve a large-scale prospective study for validation.