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Background Laparoscopic cholecystectomy (LC) is a common surgical procedure. Intraoperative findings are highly unpredictable and the operative difficulty varies from straightforward to very challenging procedures. Several studies described predictors of technical difficulty and graded intraoperative findings of LC, however none specifically reported on the effect of such factors on clinical outcomes. This study aims to evaluate the impact of patients’ preoperative characteristics on operative difficulty of LC and clinical outcomes. Methods Data of patients who underwent LC from 2015 to 2017 retrospectively analysed. Subjects were divided into four groups, according to Nassar’s classification of intraoperative difficulty. Differences in frequencies were evaluated with the Fisher’s exact test; logistic regression analysis was used to identify independent variables that were predictors of postoperative morbidity and length of stay. Results A total of 1069 patient were included. Male to female ratio of 1:2.5. Older age, male gender and comorbidities were associated with higher Nassar score (p < 0.0001); Nassar 3 and 4 were predictors of postoperative morbidity(P£0.01). The day case rate was 88.8% (Nassar 1), 86.1% (Nassar 2), 69.6% (Nassar 3), 62.3% (Nassar 4), respectively. Age of 60 and above(P£0.018), ASA 2 or 3(P£0.04) and Nassar 3, 4 (P£0.012), were predictors of increased conversion from day case to in-patient stay. Conclusion LC can be performed on a day case basis even when surgery is technically challenging. However, the need of in-patient stay can be predicted in comorbid old adult men with anticipated higher Nassar’s score.