Penile abnormalities in cheetahs (Acinonyx jubatus) are rare but can present significant challenges to both captive and wild populations. This is the first report of penile abnormalities in cheetahs, and results from the screening of 549 male individuals from 1994 to 2023. Four cases of penile abnormalities were identified and included three types of penile abnormalities: one case of frenulum persistence, one case of paraphimosis, and two cases of penile–preputial adherence. Their clinical presentation and treatment are described here. The diagnostic workup for each case involved a combination of physical examinations and anesthesia-assisted evaluations. Treatment strategies varied depending on the specific penile abnormality, but all included surgical intervention and supportive care. Through these case reports, it becomes evident that penile abnormalities in cheetahs, while rare, can manifest in different forms. Underlying causes are as yet unknown for the cheetah. Breeding decisions need to be tailored to individual cases and include consideration of the overall genetic value of the individual to the population relative to the risk of the abnormality potentially including an inheritable component. Penile abnormalities have the potential to affect the reproductive health and overall well-being of affected animals; hence early detection, accurate diagnosis, and timely interventions are crucial for successful management and treatment. These multiple case reports emphasize the need for further research on penile abnormalities in cheetahs to enhance our understanding of the underlying causes, risk factors, and potential long-term implications.