This is a prospective analysis on 30 physically active individuals with a mean age of 48.9 years (35 to 64) with chronic insertional tendinopathy of the tendo Achillis. Using a transverse incision, the tendon was debrided and an osteotomy of the posterosuperior corner of the calcaneus was performed in all patients. At a minimum post-operative followup of three years, the Victorian Institute of Sports Assessment scale -Achilles tendon scores were significantly improved compared to the baseline status. In two patients a superficial infection of the wound developed which resolved on antibiotics. There were no other wound complications, no nerve related complications, and no secondary avulsions of the tendo Achillis. In all, 26 patients had returned to their pre-injury level of activity and the remaining four modified their sporting activity. At the last appointment, the mean pain threshold and the mean post-operative tenderness were also significantly improved from the baseline (p < 0.001). In patients with insertional tendo Achillis a transverse incision allows a wide exposure and adequate debridement of the tendo Achillis insertion, less softtissue injury from aggressive retraction and a safe osteotomy of the posterosuperior corner of the calcaneum.In insertional Achilles tendinopathy, symptoms occur at the bone-tendon junction. The distal portion is affected in 24% of patients, 1 but the actual incidence of insertional Achilles tendinopathy is unknown. Conservative measures are helpful in most patients, and include rest, ice, non-steroidal anti-inflammatory drugs, careful selection of footwear and activity modification. 2 Eccentric exercises of the gastro-soleus complex are effective in only 32% of patients, with 67% of promising clinical results in patients undergoing a new model of painful eccentric calf-muscle training. 3