We report a case of primary lymphedema complicated by leaking chylous vesicles in the toe and scrotum, caused by lymphangiectasia, which was eventually managed with lymphaticovenular anastomoses after conservative treatments proved ineffective. The patient was a 25-year-old man with a 5-year history of massive swelling with chylous weeping of his right leg and scrotum. Lymphangioscintigraphy (LAS) showed dilated iliac lymph trunks causing lymph reflux. Although he was instructed in standard methods of complex therapy, it did not alleviate his symptoms. Because of the increasing frequency of cellulitis, lymphatic surgery was finally indicated. The operation consisted of lymphaticovenous anastomoses (LVA) in the ankle and groin, using a super-micro-surgical technique. After surgery, his symptoms resolved and have been controlled by self-care. Thus, early LAS to confirm the dilated iliac lymph trunks causing lymph reflux, followed by LVA might be beneficial for the management of this disease.