49 patients over the age of 50 undergoing surgical treatment for chronic insertional Achilles tendinopathy were randomly assigned to receive Achilles debridement alone or in conjunction with a flexor hallucis longus (FHL) tendon transfer. The purpose of this study was to determine whether the addition of FHL tendon transfer to the conventional Achilles debridement procedure further reduced pain and improved function up to 1 year post-operative. Outcomes were assessed using the American Orthopaedic Foot & Ankle Society (AOFAS) ankle/hindfoot score, a visual analogue scale (VAS) for pain, a patient satisfaction survey, and ankle and hallux plantar flexion strength. No significant difference between groups was observed for AOFAS ankle/hindfoot score, VAS for pain, or patient satisfaction. Significantly greater improvement to ankle plantar flexion strength was found in the FHL group.