External iliac artery (EIA) dissection and especially bilateral involvement is very rare. We report the case of a 49-year-old male intense bicyclist who had presented a dissection of the left EIA responsible for claudication. He underwent an iliofemoral vein graft bypass. The histopathologic examination showed a dissection of the EIA with an otherwise normal arterial wall. Two years after he resumed his sporting activity, a dissection of the right EIA occurred with the onset of claudication. The patient underwent a right iliofemoral vein graft bypass. Histopathologic examination showed the same lesions as on the left side. Bilateral involvement of EIA dissection is possible especially when the mechanism leading to dissection is persistent. An attentive follow-up is thus to consider.