An association between chronic venous insufficiency (CVI) and osteoarthrosis (OA) of the knee and ankle–foot joints was well known a few decades ago but subsequently forgotten. Clinical observations of the association of CVI and OA led us to prospectively study 197 consecutive patients to establish this relationship. A total of 197 patients presenting at the out-patient department of a tertiary care referral from April 2019 to March 2020 were considered after ethics committee approval. Patients were studied by clinical history, X-ray imaging, and color Doppler examination. All patients underwent definitive, obliterative treatment of the superficial venous reflux. Standard adjuvant treatment was given, and patients were re-assessed at 3 and 6 months. Outcomes were measured to find an association with CVI and OA. A direct association was found between severity of CVI and OA. Relief of symptoms of CVI and improvement in quality of life was seen at the end of 6 months. Differential diagnosis for CVI in patients complaining of knee pain, heavy legs, and swelling should always be considered and investigated. Early treatment for CVI can help preserve knee function and joint architecture. Phleboarthrosis is a real condition, and its recognition assumes greater importance with increase in life expectancy and lifestyle expectations.