Background Obstetrics and gynecology (OB/GYN) residency program websites are essential resources for applicants when selecting a residency program. Assessing these websites against a 58-point criterion can provide program administrators with actionable insights to enhance their content and make them more informative for applicants. Objective This study aims to evaluate the comprehensiveness of content on American OB/GYN residency program websites. Methods We reviewed American OB/GYN residency program websites listed on the Fellowship and Residency Electronic Interactive Database (FRIEDA). A 58-point criterion was developed based on the Accreditation Council for Graduate Medical Education (ACGME) common program requirements and prior studies. The criteria included seven categories. Programs without a webpage, military-based programs, and non-US-based programs were excluded. Results A total of 272 program websites met the inclusion criteria. On average, websites contained only 28 of the 58 study criteria (48.6%). The most commonly included information was the residency manual (59.1%), while details about didactics and program structure were the least commonly included (40.7%). Conclusion The majority of American OB/GYN residency program websites lack comprehensive information for applicants. Residency programs should consider incorporating key details such as application information, introduction to the program, residency manual, didactics and program description, research, current resident information, and graduate/post-residency placement.