Introduction: T-tube placement during liver transplantation (LT) is still debated. We performed a retrospective study to evaluate the usefulness of T-tube after LT in two cohorts differing in post-transplant risk. Methods: A total of 327 LTs performed between 2015 and 2018 were included in the analysis. LTs from donation after circulatory death and living donation, split-liver transplants, and LTs with hepaticojejunostomy were excluded. T-tube was reserved for marginal grafts, high-risk recipients, and bile duct size discrepancy. A balance of risk (BAR) score of ≤9 defined the low-risk cohort (232 patients, 68 with and 164 without T-tube), while a BAR score of >9 defined the high-risk cohort (95 patients, 43 with and 52 without T-tube). Postoperative complications were estimated with the comprehensive complication index (CCI). Postoperative biliary complications were classified in anastomotic stricture (AS), non-anastomotic stricture (NAS), and biliary leakage (BL). Results: In the low-risk cohort, LTs with and without T-tube had similar rates of NAS (0 vs. 2.9%, p = 0.36), AS (2.9 vs. 2.4%, p = 0.83), and BL (1.4 vs. 2.4%, p = 0.64). Analogous outcomes were found in the high-risk cohort: NAS (0 vs. 0), AS (0 vs. 5.7%, p = 0.11), and BL (0 vs. 1.3%, p = 0.27). There were more postoperative complications among patients with T-tube, in both the low-risk (CCI 29 vs. 21, p < 0.001) and high-risk (CCI 51 vs. 29, p < 0.001) cohort. No differences in primary non-function, hepatic artery thrombosis, and mortality were observed. Conclusions: T-tube placement did not influence postoperative biliary complications. Although the two cohorts were normalized for post-transplant risk, LT recipients with T-tube had a more complicated course.