© 2020 American Association of Oral and Maxillofacial Surgeons Purpose: The purpose of this study was to compare length of hospital stay and opioid usage among head and neck surgery (HNS) patients treated with and without regional anesthesia for microvascular free-flap donor sites. Methods: The authors performed a retrospective cohort study for HNS patients undergoing microvascular free-flap reconstruction. The control group received no regional anesthesia. The experimental group had a regional anesthesia nerve block performed immediately before surgery. The primary outcome variable was length of stay, and the secondary outcome variable was total morphine milliequivalents. The data were analyzed using Student t tests, analysis of variance, Mann-Whitney U test, Kruskal-Wallis test, χ2 test, and multiple linear regression. Results: The study sample was composed of 148 patients with a mean age of 58.1 years. The mean length of stay for the control group was 6.74 ± 1.57 days, compared with the experimental group at 5.84 ± 1.01 days (P <.0001). The mean morphine milliequivalent was 256.5 ± 164.6 mg for the control group and 208.9 ± 164.8 mg for the experimental group (P =.56). Importantly, the demographics, pathology spectrum, flap selection, duration of procedure, and complication rate were similar in both groups. Conclusions: This study demonstrates that for HNS patients undergoing microvascular reconstruction, regional nerve block at the donor site is associated with significantly shorter hospital stays. Although there was a trend toward decreased opioid usage in the regional anesthesia group, these results did not reach statistical significance. Consideration should be given to incorporate regional anesthesia techniques into early recovery after surgery protocols for centers performing high-volume head and neck microvascular reconstruction.