This study aims to determine the prevalence and characteristics of bilateral osteochondritis dissecans of the knee in patients presenting with unilateral symptoms and compare this cohort to patients with unilateral disease. Records of patients ≤18 years old from 2003 to 2016 with a diagnosis of osteochondritis dissecans of the knee and strictly unilateral knee pain were identified. Contralateral (asymptomatic) knee imaging within 1 year of initial presentation was required. Lesion characteristics were evaluated by assessing size, location, and Hefti staging. Both surgical and nonoperative treatments were recorded. Patients with unilateral osteochondritis dissecans were compared to those with bilateral disease. Eighty patients, 63 males (79%) and 17 females (21%), with an average age of 13.1 years old, were included. Twenty (25%) of the presenting/symptomatic lesions were deemed stable on magnetic resonance imaging. A positive correlation between lesion size and Hefti classification was appreciated. Twelve patients (15%) were found to have bilateral osteochondritis dissecans on contralateral imaging. There was no significant difference in skeletal maturity between patients with bilateral versus unilateral disease. Fifty-two patients (77%) with unilateral disease underwent surgical intervention, while 9 (75%) of those with bilateral disease underwent surgery on either knee. In patients with an asymptomatic contralateral lesion, 67% ultimately underwent surgical intervention on the contralateral knee. In patients presenting with unilateral osteochondritis dissecans symptoms, there was a 15% prevalence of bilateral disease, with no difference in age, sex, physeal status, or lesion characteristics between patients with unilateral vs bilateral osteochondritis dissecans lesions. Given the prevalence of asymptomatic contralateral lesions and the required intervention, this study supports early bilateral radiologic knee evaluation. IV, Retrospective Case series.