Bilateral stress fracture of the tibia is infrequent. This paper presents an unusual case of a 73-year-old man who sustained a bilateral stress fracture of the tibia presenting as painful edemas in lower limbs. The radiographic and scintigraphic examination confirmed the diagnosis of the fractures. In addition, the patient was receiving androgen deprivation therapy with GnRH analogs for the treatment of prostate cancer and the bone density measurements confirmed the presence of osteoporosis. Treatment with restricted weight bearing was associated with improvement of clinical symptoms. Early recognition and diagnosis of this injury is essential for treating the underlying osteoporosis as well as the fracture.