Phlegmasia cerulea dolens is a rare and severe form of deep venous thrombosis (DVT), characterized by an extensive thrombus burden and compromised venous outflow. We present the case of a 28-year-old male with a history of bilateral lower extremity DVTs and multiple venous stents who presented with acute-onset pain and swelling in the left lower extremity. Diagnostic imaging confirmed an acute DVT extending throughout the left lower extremity, including the external iliac vein. Given the diagnosis of phlegmasia cerulea dolens, a multidisciplinary approach involving interventional cardiology, orthopedic surgery, and vascular surgery was adopted. Intravascular ultrasound (IVUS)-guided thrombus removal and angioplasty were performed to restore venous outflow and improve limb perfusion. The procedure successfully removed a significant amount of thrombus and improved flow throughout the venous system. The patient exhibited an excellent clinical response, with pain resolution and improved perfusion. This case highlights the challenges and effectiveness of a combined intervention in managing complex phlegmasia cerulea dolens cases with previous venous stents.