Chronic Achilles pain is a pathological condition with long lasting—more than six weeks—pain in the Achilles tendon mid-portion or insertion with signs of tendinopathic changes. Participation in sports, which predominantly feature running and jumping, increases the lifetime risk of Achilles tendinopathy up to 52%. The diagnosis is predominantly clinical, although there is a role for radiography, ultrasonography, computed tomography, and magnetic resonance imaging. Dysfunction and decreased physical performance, together with swelling and painful fusiform thickening are the most common clinical symptoms and signs. Neovascularization in the mid-portion, tendon ossification, bone spurs, retrocalcaneal and subcutaneous bursitis, and posterosuperior calcaneal prominence at the insertional region are also common signs of chronic pathology. Non-surgical treatment consisting of eccentric exercise is the first line of treatment, followed by orthoses, rest, NSAIDs (non-steroidal anti-inflammatory drugs), and extracorporeal shock-wave therapy. High-volume injection of local anesthetic and saline has a mechanical stripping effect when placed anterior to a tendinopathic tendon; the complication risk is low. Endoscopic debridement, with plantaris tendon resection, has shown promising results in patients with symptoms unresponsive to non-surgical treatments for mid-portion pathology. Resection of the posterosuperior calcaneal prominence with bursectomy and endoscopic or mini-open removal of calcifications in patients with Achilles insertional tendinopathy has shown good results and low complication rate.