Obstetric and gynecologic (OB/GYN) physicians are frequently involved in malpractice lawsuits, some of which result in catastrophic payouts. This study categorized malpractice claims involving OB/GYN trainees (students, residents, and fellows) between 1986 and 2020. Cases are categorized by type of injury, patient outcome, category of error, outcome of lawsuit, and amount of settlement.