Objective The aim of this study is to assess the impact of a prolonged second stage of labor on maternal and neonatal outcomes by comparing women who had expectant management versus operative intervention beyond specified timeframes in the second stage of labor. Study Design Retrospective cohort including live singletons at ≥36 weeks who reached the second stage of labor. Expectant management (second stage >3, 2, 2, and 1 hour in nulliparas with an epidural, nulliparas without an epidural, multiparas with an epidural, and multiparas without an epidural, respectively) was compared with those who had an operative delivery (vaginal or cesarean) prior to these timeframes. The primary maternal outcome was a composite of postpartum hemorrhage, chorioamnionitis, operative complications, postpartum infections, and intensive care unit admission. The primary neonatal outcome was a composite of cord blood acidemia, 5-minute Apgar's score <5, chest compressions or intubation at birth, sepsis, seizures, birth injury, death, transfer to a long-term care facility, and respiratory support for >1 day. Results Among 218 women, 115 (52.8%) had expectant management. Expectant management was associated with a significantly increased risk of the maternal composite (adjusted odds ratio [aOR]: 1.99, 95% confidence interval [CI]: 1.09-3.64) but not the neonatal composite (aOR: 1.54, 95% CI: 0.71-3.35). Conclusion Expectant management of a prolonged second stage was associated with a higher rate of adverse maternal outcomes, but the rate of adverse neonatal outcomes was not significantly increased.