Since its first description in 1879, popliteal arteryentrapment syndrome remains a debilitating condition,which frequently affects young active people. Increasedawareness of popliteal artery entrapment syndromecombined with improvements in investigative modalitieshas resulted in a more frequent diagnosis of thiseminently treatable condition. In this article, a rarecase of bilateral popliteal artery entrapment syndromein a physically active 33-year-old man precipitated bycompetitive Bicycle Moto-Cross riding is presented. Ahigher index of suspicion for popliteal artery entrapmentsyndrome is recommended as the underlyingpathology in a young active person with symptoms oflower limb claudication. Popliteal artery entrapmentsyndrome should be investigated with thorough radiologicalassessment prior to any therapeutic intervention,which is often fraught with difficulty due tochronically diseased vasculature and inherent anatomicalanomalies.