Objective: Today laparoscopic cholecystectomy (LC) is the treatment of choice for acute cholecystitis. However, the presence of severe inflammation makes it challenging for the surgeons to accurately recognize the Calot’s triangle which increases the risk of intraoperative complications. The aim of this study was to explore the validity of a scoring system used to predict difficult LC and to analyse the risk factors associated with difficult cholecystectomy in the setting of acute calculous cholecystitis. Material and Methods: An observational study was conducted between December 2018 and December 2020 among 132 patients diagnosed with acute cholecystitis, who underwent laparoscopic cholecystectomy. A scoring system by Randhawa et al. was used preoperatively for all of these patients to predict difficult LC, which was correlated to intraoperative difficulties in actual surgery. Data were analysed using the SPSS version 26.0. Results: Mean age was 43.63 ± 13.37, with almost equal representation from both sexes. History of previous attacks of cholecystitis, impacted stone, thickness of GB wall were statistically significant in calculating preoperative difficulty of laparoscopic cholecystectomy. The scoring system had a sensitivity and specificity of 82.6% and 63.5%, respectively. The conversion rate to open cholecystectomy was 6.9%. Conclusion: Analysing the significant risk factors before operating in the presence of an inflamed gallbladder can reduce the overall mortality and morbidity. An accurate preoperative scoring system will enable the operating surgeon to be well prepared with adequate resources and time. The patient attenders can also be counselled regarding the risk involved beforehand.