Surgical treatment of chronic Achilles tendon rupture is a technically challenging procedure. We aimed to compare the clinical outcomes, range of motion, and strength of ankle plantar- and dorsiflexors between two techniques for fixation of flexor hallucis longus tendon to the calcaneus: interference screw and suture-external button. Twenty-five patients participated in this retrospective comparative study. All patients underwent short harvest FHL tendon transfer for chronic AT rupture were asked for a follow-up visit, at least one year following surgery. The outcomes were evaluated by visual analog scale (VAS), AOFAS ankle-hindfoot score, and VISA-A questionnaire. Ankle ROM with possible restriction in addition to isokinetic strength of ankle plantar- and dorsiflexors was assessed. No statistically significant difference was observed between the groups for pain (P = 0.81), AOFAS ankle-hindfoot scale (P = 0.97), and VISA-A (P = 0.44). Notably, more decrease in ankle dorsiflexion was seen in interference screw group in comparison with suture-external button group (4.4 ± 6.6 vs. 9.5 ± 6.1 degrees, P = 0.06). The difference of active dorsiflexion between operated and non-operated side in interference screw group was statistically significant (P = 0.02). Biotenodesis screw imposed more limb asymmetry in comparison with suture-external button technique. Fixation of transcalcaneal FHL tendon transfer for chronic AT either by interference screw or suture-external button has encouraging postoperative clinical results. Although ROM of the ankle joint reduced in both techniques, interference screw may result in more reduction in dorsiflexion of the ankle.