Popliteal artery entrapment syndrome (PAES) is a rare but important cause of leg ischemia and even disability in young athletes. Entrapment occurs because of an abnormal relationship between the popliteal artery and the surrounding muscular structures in the popliteal fossa. These anomalies lead to decreased blood flow to the affected leg with signs of claudication, coldness, and symptoms of exercise-induced leg pain. In this article, we present a case of a young soldier who presented with the above signs and symptoms in his left foot after exercise. On questioning, he admitted to having chronic lower leg pain. He was diagnosed with PAES in both legs and he was emergently treated with an arterial bypass procedure in the left one. He had no postoperative complications. PAES should be considered in the differential diagnosis of chronic or acute lower leg pain in any young patient. Early diagnosis and treatment can prevent limb loss and lead to a good operative outcome.