Setting: Academic outpatient physiatric private practice. Patient: A 53-year-old man. Case Description: The patient presented with complaints of left posterior thigh and knee pain and hematoma 4 days after twisting his left leg. He developed buttock pain, followed by a “baseball-sized” gluteal mass, both of which resolved over the next 2 days. Physical findings included tenderness to palpation over the ischial tuberosity, large ecchymosis, and swelling suggestive of hematoma extending from the left gluteal area to the calf. Neurologic exam was normal except for mild left hamstring weakness. Assessment/Results: Clinical presentation was consistent with hamstring injury with hematoma formation. Radiographs of the pelvis were negative for hamstring avulsion, however, they demonstrated the incidental findings of calcifications over the neck of the femur, suggestive of cartilaginous lesions. Subsequent magnetic resonance imaging demonstrated a large osteochondroma and a large, partially ruptured bursa formation with intact hamstrings, fluid collection causing partial encasement of the sciatic nerve, and effacement of the proximal hamstrings, gluteus maximus, and adductus magnus. Discussion: This is the first reported case, to our knowledge, of osteochondroma of the femur associated with large bursa formation presenting as hamstring injury in an older patient. Osteochondroma is a common tumor, which usually presents in adolescence. Large bursa formation in association with osteochondroma of the femur is a rare complication that may represent malignant transformation and must be ruled out. Conclusion: Osteochondroma with large bursa formation can have unusual presentations, including the appearance of hamstring injury and hematoma. Presumed hamstring injuries are commonly managed conservatively and, in most cases, imaging studies do not play a significant role in the work-up. However, diagnostic imaging can play a central role in the diagnosis of bone tumors.