Objectives: Postoperative respiratory depression is of concern in children undergoing adenotonsillectomy receiving postoperative opioids and may be mitigated with intraoperative bupivacaine. This study aims to compare the impact of bupivacaine on postoperative pain and sedation in various pediatric age and surgical indication subgroups. Methods: This is a case series with chart review of 181 patients <18 years old undergoing adenotonsillectomy at a tertiary care center (2013-2016). Postoperative outcomes were compared between those who received intraoperative bupivacaine before (pre-tonsillectomy) or after (post-tonsillectomy) tonsil removal and those who did not (none) using χ2 test and analysis of variance. Subanalysis was performed after stratifying into age and surgical indication subgroups. Results: Ninety-eight patients were included in the pre-tonsillectomy group, 47 in the post-tonsillectomy group, and 36 in the none group. The number of postanesthesia care unit opioid doses ( P = .159) and pain scores at arrival ( P = .362) or discharge ( P = .255) were not significantly different between treatment groups overall. Among 0- to 5-year-olds, pre-tonsillectomy injection was associated with lowest mean (SD) discharge pain score of 0.55 (1.29) pre-tonsillectomy versus 0.71 (1.37) post-tonsillectomy versus 2 (1.63) none group ( P = .004). Among 12- to 17-year-olds, no injection was associated with lowest mean (SD) discharge pain score of 2.33 (0.52) pre-tonsillectomy versus 5 (2.65) post-tonsillectomy versus 1.63 (1.60) none group ( P = .020). Injection in patients with obstructive sleep apnea and/or sleep-disordered breathing did not improve postoperative outcomes. Conclusion: Intraoperative bupivacaine may improve pain scores in younger pediatric populations, though it may not impact the amount of postoperative opioid use. Prospective analysis with a larger sample size is warranted to better outline opioid usage and pain control in this group.