Osteochondromas are bony outgrowths covered by thin cartilaginous caps, accounting for 35% of all benign bone tumours. The majorities are solitary and usually arise at the metaphysis of long bones. They may be associated with bursa formation, while vascular complications are rare. We report a 34-year-old man who presented with a 2-week history of pain, stiffness and swelling of the left lower leg following a cricket match. Clinically, a deep vein thrombosis (DVT) was suspected but D-dimer test was negative. Initial Doppler ultrasound scan (USS) was reported as showing a haematoma and possible DVT. A repeat Doppler USS did not detect a DVT, however the popliteal vein appeared collapsed and a pedunculated osteochondroma of the proximal tibia was found. An MRI confirmed this and also showed an extensive oedema around the calf muscles tracking distally in all compartments, most likely the result of a ruptured bursa.