Avulsion fractures of the peroneus longus tendon are seldom seen and potentially can go undiagnosed during an emergency visit. If not managed appropriately, it can lead to chronic pain and suffering. This case report presents a 55-year-old postman who was seen in the clinic complaining of persistent pain over the instep of his right foot with no history of trauma. His pain was localized to the first metatarsophalangeal joint with some radiation to the heel. Magnetic resonance imaging revealed an isolated avulsion fracture of the first metatarsal, which was initially missed on X-ray. In this case, the patient was successfully treated with a mixture of steroid and local anesthetic injections. Following our intervention, the Manchester Oxford Foot Questionnaire was reduced from 33 to 0. The goal of this article is to raise awareness of this rare finding for doctors who may face this in accident and emergency (A&E), Orthopedic clinics or at a general practice (GP) practice.