Chronic pain symptoms related to the Achilles tendon, referred to as tendinopathy, are a disabling condition in the general population. Achilles midportion tendinopathy is the most frequently reported overuse injury experienced by individuals engaged in activity, particularly at recreational or competitive level. Despite recent research, the pathogenesis still remains elusive. A broad range of intrinsic and extrinsic factors, alone or in combination, is used to explain the cause of overuse injuries. Symptoms are localized to the midportion of the Achilles tendon and typically consist of pain related to activity, swelling, and impaired load bearing capacity. A multitude of structures of the Achilles tendon are implicated in the differential diagnosis. The patient’s medical history and clinical examination play a key role in the diagnosis and management.