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Introduction. Whipple’s pancreatoduodenectomy (PD) is a formidable operation, associated with a high risk of morbidity and mortality. In the setting of an underlying chronic liver disease, the incidence of complications and mortality increases manifold. Patients and Outcomes. Of the 112 Whipple’s PD performed between 2018 to 2020 at a high-volume HPB and liver transplant centre, 4 patients underwent the surgery in the background of an underlying chronic liver disease (CLD). All except one were performed in Child’s A cirrhotics. There was a single 30-day mortality in this series of 4 patients that occurred in the background of Child’s B cirrhosis. On follow-up at 1 year, there was one more mortality in the series, owing to liver decompensation following chemotherapy. Conclusion. Judicious preoperative selection criteria, adequate preoperative nutritional and physiological optimisation, and prudent weighing of risk vs. benefit of undergoing Whipple’s PD in periampullary malignancies in the setting of CLD are the major determinants of the surgical outcome.