Background Operative site drainage (OSD) after elective hepatectomy remains widely used despite data suggesting limited benefit. Multi-institutional, quality-driven databases and analytic techniques offer a unique source from which the utility of OSD can be assessed. Study Design Elective hepatectomies from the 2014 American College of Surgeons (ACS) NSQIP Targeted Hepatectomy Database were propensity score matched on the use of OSD using preoperative and intraoperative variables. The influence of OSD on the diagnosis of postoperative bile leaks, rates of subsequent intervention, and other outcomes within 30 days were assessed using paired testing. Results Operative site drainage was used in 42.2% of 2,583 eligible hepatectomies. There were 1,868 cases matched, with 7.2% experiencing a post-hepatectomy bile leak. The incidence of bile leak initially requiring intervention was no different between the OSD and no OSD groups (n = 32 vs n = 24, p = 0.278), and OSD was associated with a greater number of drainage procedures to manage post-hepatectomy bile leak (n = 27 in the OSD group, n = 13 in the no OSD group, p = 0.034, relative risk [RR] 2.1 [95% CI 1.1 to 4.0]). The OSD group had a greater mean length of stay (+0.8 days, p = 0.004) and more 30-day readmissions (p < 0.001, RR 1.6 [95% CI 1.2 to 2.1]). On multivariate analysis, post-hepatectomy bile leak and receipt of additional drainage procedures were stronger predictors of increased length of stay and readmissions than OSD. Conclusions In a propensity score matched cohort, OSD did not improve the rate of diagnosis of major bile leaks and was associated with increased interventions, greater length of stay, and more 30-day readmissions. These data suggest that routine OSD after elective hepatectomy may not be helpful in capturing clinically relevant bile leaks and has additional consequences.