Background Osteochondritis dissecans (OCD) rarely occurs in multiple joints. Furthermore, the existence of left-right asymmetric OCDs in different joints of the contralateral side of the body and lesions occurring with a temporal difference is rare. Here, we report a rare case with multiple OCDs sequentially detected in various joints. Case Presentation . The 15-year-old male patient was referred to our hospital for an OCD in the medial femoral condyle of the left knee. He had a history of an OCD in his right elbow, and his father had a history of surgically treated OCDs in both knees. One year and five months after, surgery was performed to the lesion in his left medial femoral condyle, a new OCD lesion occurred in the femoral trochlea of the same knee, which was again treated surgically. Five months after the second surgery, the patient returned with pain in the right knee, and an OCD on the right femoral trochlea was detected by an MRI scan. This lesion remained stable without any further restriction in physical activities for 17 months until detachment occurred and was again treated surgically. Conclusion In cases with history and a family history of multiple OCDs, in particular, with a short stature, an MRI scan should be performed for the symptomatic joint to detect and treat the lesion before progression.