Purpose: To report a case of a 79-year-old man who presented a bilateral popliteal artery aneurysm compressing both popliteal veins mimicking signs and symptoms of post-thrombotic syndrome. Case Report: A 79-year-old male patient, was seen in the ambulatory clinic with a 2-year history of bilateral leg swelling, calf pain, chronic ulceration, and hyperpigmentation. Upon physical examination, lower extremities were edematous, with a 3 cm suppurative ulcer on each leg. Image studies showed a popliteal right arterial aneurysm of maximum diameter of 41.7 mm, extrinsically compressing the ipsilateral popliteal vein. Likewise, on the left leg, a popliteal arterial aneurysm of maximum diameter of 47.9 mm was encountered triggering the same phenomenon. Bilateral endovascular treatment deploying stent grafts was auspiciously performed. At 36-months follow up, his symptoms are completely resolved, and his ulcers healed. US follow up showed exclusion of the aneurysms with progressive shrinkage of both residual sacs. Conclusion: Popliteal artery aneurysm compressing and constraining flow in the popliteal vein must be included as a differential diagnosis among the causes of chronic venous syndromes. Prompt diagnosis with its appropriate treatment is needed for reducing severe complications caused by PAA, such as the venous disorder our patient had.