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Iliac artery occlusion in patients with complex anatomical variations, such as a horseshoe kidney and severe aortic calcification, presents unique challenges to standard revascularisation techniques. In such scenarios, conventional aortobifemoral bypass may carry significant risks due to difficult aortic access and the potential for renal injury. This case describes a man in his early 50s with right common iliac artery occlusion, anterior aortic calcification and a horseshoe kidney, where an extra-anatomic left common iliac to right superficial femoral artery bypass using a polytetrafluoroethylene graft was performed. The approach successfully restored limb perfusion while avoiding high-risk aortic manipulation. Postoperative recovery was uneventful, with improved symptoms and maintained graft patency. This case underscores the importance of individualised surgical planning and highlights extra-anatomic bypass as a safe and effective alternative in anatomically complex patients.