Purpose: Most patients undergoing index admission cholecystectomy (ILC) have some degree of acute liver function abnormality. Aging males have a threefold incidence of background liver dysfunction. This study was designed to quantify the perioperative impact of males over fifty with evidence of liver damage (ELD). Methodology: ILC cases performed at Middlemore Hospital in 2022 were retrospectively analysed. A patient subgroup including men over 50 with ELD was compared to the remaining cohort. Four outcomes were analysed: Length of stay (LOS), operating time (OT), number of investigations, and major complications. Statistical methods included independent t-tests, Fisher’s exact test, and multivariate regression modelling. Results: Of 457 patients who underwent ILC, 66 patients were men over 50 with ELD. The 391 remaining patients were the comparison group. Men over 50 with ELD experienced a longer LOS (MD 1.57 days, p = 0.002, 95% CI 0.58 to 2.56 days), longer OT (MD 9.22 minutes, p = 0.027, 95% CI 1.05 to 17.39 minutes), underwent more investigations (MD 2.77 investigations, p = 0.00045, 95% CI) and had increased odds of a major complication (OR = 3.02, p = 0.018, 95% 1.08 to 7.81). Multivariate linear regression models were significant for LOS (p < 0.0001), OT (p = 0.0016) and number of investigations (p < 0.0001). Conclusion: Men over 50 with ELD experienced increased LOS, OT, number of investigations, and had an increased likelihood of a major complication when undergoing ILC. Acute service co-ordination and peri-operative counselling for these patients should factor in these results and the increased likelihood of deviation from routine recovery.