Background: A large number of ruptures of the Achilles tendon occurs in the watershed hypovascular region (zone II) of the tendon which is approximately 2–6 cm proximal to the insertion of tendon at calcaneum. Chronic Achilles tendon rupture in the watershed area makes end to end repair of tendon less feasible and the neglected distal stump is often inapt for repair. A number of surgical techniques have been described for repair of chronic Achilles tendon in zone II. Our study was conducted with the objective of determining the efficacy and functional outcome of Bosworth’s technique that involves gastrocnemius-soleus turndown of proximal Achilles tendon. Materials and Methods: The study was conducted in a total of five patients with chronic tear of Achilles tendon and the Bosworth technique was used for repair in all the patients. All the patients were followed up for a period of 1 year and the functional outcome was assessed by scoring system devised by Leppilahti et al. Results: four out of the five patients showed excellent functional at the end of 1 year follow up. A good functional outcome was seen in one of the patients. All the patients were able to resume work 6 months postoperatively. Conclusion: The Bosworth’s technique is an excellent surgical procedure for repair of chronic Achilles tendon rupture in the watershed zone of the tendon.