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BACKGROUND Incidence of gallstones in those aged ≥ 80 years is as high as 38%-53%. The decision-making process to select those oldest old patients who could benefit from cholecystectomy is challenging. AIM To assess the risk of morbidity of the “oldest-old” patients treated with cholecystectomy in order to provide useful data that could help surgeons in the decision-making process leading to surgery in this population. METHODS A retrospective study was conducted between 2010 and 2019. Perioperative variables were collected and compared between patients who had postoperative complications. A model was created and tested to predict severe postoperative morbidity. RESULTS The 269 patients were included in the study (193 complicated). The 9.7% of complications were grade 3 or 4 according to the Clavien-Dindo classification. Bilirubin levels were lower in patients who did not have any postoperative complications. American Society of Anesthesiologists scale 4 patients, performing a choledocholithotomy and bilirubin levels were associated with Clavien-Dindo > 2 complications (P < 0.001). The decision curve analysis showed that the proposed model had a higher net benefit than the treating all/none options between threshold probabilities of 11% and 32% of developing a severe complication. CONCLUSION Patients with American Society of Anesthesiologists scale 4, higher level of bilirubin and need of choledocholithotomy are at the highest risk of a severely complicated postoperative course. Alternative endoscopic or percutaneous treatments should be considered in this subgroup of octogenarians.