Purpose: To determine the feasibility of synchronous superficial venous surgery and on-table subintimal angioplasty in the treatment of venous ulcers with arterial compromise. Methods: Between January 1992 and December 2004, 9 patients (8 women; median age 83 years, range 72–92) underwent the synchronous procedure. No patient had deep venous reflux; 4 patients presented with rest pain and 2 were diabetic. Their medical records were retrospectively reviewed to gather data on clinical assessment, ankle-brachial index (ABI), lower limb arterial and venous duplex scans, and treatment variables. Results: Angioplasty was technically successful (median ABI improvement 0.31, range 0.23–0.34) in all procedures, which lasted a median 85 minutes (range 60–160). The procedure was performed under general anesthesia in 7 patients, local in 1, and spinal in 1. Superficial venous surgery was performed first in 8 patients: 6 had great saphenous vein (GSV) ligation without stripping, followed by subintimal angioplasty, and 1 also had small saphenous vein (SSV) ligation. One patient underwent SSV ligation first, followed by angioplasty; another had GSV disconnection and stripping, followed by angioplasty. In 1 patient, angioplasty preceded GSV surgery. One patient required repeat angioplasty 1 week later for re-occlusion. All ulcers healed (median 4 months, range 1–36). Five patients died during a median 32-month follow-up (range 4–82) from unrelated causes; there was 1 ulcer recurrence at 3 years in a patient who declined further investigation and treatment. Conclusions: Simultaneous superficial venous surgery and on-table subintimal angioplasty is a safe and novel strategy in the management of a select subgroup of patients with venous ulcers and coexistent arterial compromise.