A chronic Achilles tendon rupture is a tendon rupture occurring more than 4–6 weeks after a traumatic injury. Haglund’s deformity, caused by bony abnormalities in the ankle (mostly due to osteophyte or bone spur), can cause chronic inflammation and degeneration of the Achilles tendon, eventually leading to rupture. This presents a challenge for clinicians who provide tendon repair procedures. We present a 69-year-old woman who had difficulty moving her left leg and had a deformity on the left leg compared to her right leg after falling nine months before but with pain starting three months before the accident. There was a seven-centimeter gap in the calcaneus with a positive Thompson test. The Haglund’s deformity on the left calcaneus was visible on the ankle X-ray. The patient had a chronic total rupture of the left Achilles tendon, which was treated with a flexor hallucis longus (FHL) tendon transfer and resection of the deformity. One week after surgery, the patient’s ability to walk and the shape of the left leg improved. This case report describes a chronic left Achilles tendon condition that was successfully repaired through tendon repair surgery using FHL tendon transfer and removal of Haglund’s deformity.