Background: While the liability risks for obstetrics and gynecology (ob/gyn) physicians are widely recognized, little is known about how trainees have been involved in ob/gyn lawsuits. Objectives: To characterize involvement of trainees in malpractice lawsuits related to ob/gyn. Methods: The legal database Westlaw was utilized to collect ob/gyn-related malpractice lawsuits involving trainees reported from 1986 to 2020 in the USA. Outcome: Forty-six malpractice cases involving ob/gyn trainees were identified, including 34 cases related to obstetrics and 12 to gynecology. There were 11 cases alleging lack of informed consent, including 7 cases alleging lack of consent for trainee involvement. Of the 34 obstetrics cases, 27 related to procedural complications, 17 to treatment, 13 to diagnosis, and 4 to informed consent. Of these, 17 were decided in favor of the physician, 6 resulted in findings of negligence, 9 had unknown outcomes, and 3 ended in settlement. For the 6 cases ending in a finding of negligence, the mean award was $2,174,472 compared to $685,000 for those that were settled. Of the 12 gynecology cases, 8 related to procedural complications, 7 to informed consent, 3 to diagnosis, and 2 to treatment. Of these, 6 were decided in favor of the physician, 3 resulted in findings of negligence, and 3 had unknown outcomes. For the cases ending in a finding of negligence, the mean award was $465,000. Conclusions and Outlook: This review of malpractice cases highlights types of situations in which trainees are sued and reveals the importance of designing curriculum around faculty training and supervision regarding trainee involvement in patient care.