Osteochondroma, the most common tumor of bone, is usually asymptomatic. Vascular complications are an atypical presentation and include true or false aneurysm formation, deep venous thrombosis, and arterial insufficiency. A review of the English literature identified 130 cases of osteochondroma-related vascular complications. We describe the case of a 38-year-old man presenting with left calf pain and swelling who was diagnosed with the rare constellation of a popliteal pseudoaneurysm and incidental peroneal vein thrombosis secondary to a fractured femoral sessile osteochondroma. This was treated with resection of the osteochondroma, excision of the aneurysm, and primary end-to-end anastomosis of the artery.