This case study reports the diagnosis and treatment of a lower limb venous ulcer with abnormal underlying venous pathology. One male patient presented with bilateral varicose veins and a right lower limb ulcer. Upon investigation, full-leg duplex ultrasonography revealed total incompetence of the great saphenous vein in the left leg. In the right leg, duplex ultrasonography showed proximal incompetence of the small saphenous vein, and dilation of the anterior accessory saphenous vein, which remained competent. Incidentally, two venous collaterals connected onto the distal region of both these segments, emerging from a scarred, atrophic popliteal-femoral segment. An interventional radiologist performed venoplasty to this popliteal-femoral venous segment. Intervention was successful and 10 weeks post procedure ulceration healed. Popliteal-femoral venous stenosis may be associated with venous ulceration in some cases and may be successfully treated with balloon venoplasty intervention.