Insertional Achilles tendinopathy is a frequent cause of pain and performance impairment of the ankle. It is more common in runners, but may also affect general population. Conservative treatment is the gold standard in the early phases but 10% to 30% of patients require surgery. The aim of this study is to review the current literature in order to evaluate current surgical strategies for Insertional Achilles tendinopathy and to analyze the effectiveness of the available techniques. We performed a systematic review of the literature, to identify studies reporting clinical outcome after surgical treatment for Insertional Achilles tendinopathy in any population group with at least 6 months follow-up. The quality of the articles included was evaluated by the Coleman Methodology Score and correlated with the reported outcome and year of publication. We identified 16 studies reporting on 465 surgically treated Insertional Achilles tendinopathy with a mean follow-up of 29.8 months. Average age at the time of surgery was 53 years. Two different categories of surgical treatment were distinct: debridement alone or debridement with augmentation in case of excessive tendon loss. Results were excellent or good in 89.6% of cases and fair or poor in 10.4%. Average complications rate was 18.3%, with 15.7% of minor and 2.6% of major complications with no difference in the two groups. Negative correlation was found between Coleman Methodology Score and the reported outcome and positive correlation was found between Coleman Methodology Score and year of publication. Good or excellent outcome can be expected after surgical treatment for Insertional Achilles tendinopathy whatever the adopted procedure, but there is no specific evidence regarding which surgical technique provides a better outcome or a lower rate of complications. Research with higher levels of evidence and methodology that is more rigorous are needed in order to evaluate the optimal surgical strategy for patients with IAT.