Livedoid vasculopathy (LV) is a hyalinizing vascular disease characterized by painful purple macules and papules that subsequently ulcerate. This vasculopathy may be associated with chronic venous insufficiency, deep venous thrombosis, factor V Leiden mutation, protein C deficiency, antiphospholipid syndrome, increased homocysteine levels, abnormalities in fibrinolysis, increased platelet activation and sickle cell disease. Difficult venous access, unreliable measurement of peripheral O2 saturation and increased susceptibility to venous embolic events may be a challenge for anesthetists. There is limited data about anesthetic management of livedoid vasculopathy in the literature. This case report describes successful anesthetic management of two patients with livedoid vasculopathy.