Background Insertional Achilles tendinopathy is well known to be difficult to treat, especially when there is intra-tendinous bone pathology. This study is a case series on patients with chronic insertional Achilles tendon pain and major intra-tendinous bony pathology together with bursa and tendon pathology, treated with excision of the subcutaneous bursa alone. Methods Eleven patients (eight men and three women) with a mean age of 44 years (range 24-62) and a chronic (>6 months) painful condition from altogether 15 Achilles tendon insertions were included. In all patients, ultrasound examination showed intra-tendinous bone pathology together with pathology in the tendon and subcutaneous bursa, and all were surgically treated with an open excision of the whole subcutaneous bursa alone. This was followed by full weight-bearing walking in a shoe with open heel for 6 weeks. Results At follow-up 21 (median, range 12-108) months after surgery, 9/11 patients (12/15 tendons) were satisfied with the result of the operation and 10/11 (13/15 tendons) were back in their previous sport and recreational activities. The median VISA-A score had improved from 41 (range 0-52) to 91 (range 33-100) (p<0.01). Conclusion In patients with chronic painful insertional Achilles tendinopathy with intra-tendinous bone pathology, tendon and bursa pathology, open removal of the subcutaneous bursa alone can relieve the pain and allow for Achilles tendon loading activities. The results in this case series highlight the need for more studies on the pain mechanisms in insertional Achilles tendinopathy and the need for randomised studies to strengthen the conclusions.