Since its first description in 1879, popliteal artery entrapment syndrome remains a debilitating condition, which frequently affects young active people. Increased awareness of popliteal artery entrapment syndrome combined with improvements in investigative modalities has resulted in a more frequent diagnosis of this eminently treatable condition. In this article, a rare case of bilateral popliteal artery entrapment syndrome in a physically active 33-year-old man precipitated by competitive Bicycle Moto-Cross riding is presented. A higher index of suspicion for popliteal artery entrapment syndrome is recommended as the underlying pathology in a young active person with symptoms of lower limb claudication. Popliteal artery entrapment syndrome should be investigated with thorough radiological assessment prior to any therapeutic intervention, which is often fraught with difficulty due to chronically diseased vasculature and inherent anatomical anomalies.