Injuries to the medial side of the knee can occur in isolation or in conjunction with multiple other ligaments about the knee. In addition, medial knee injuries can involve isolated injury to the medial collateral ligament or include the posteromedial structures of the knee. Treatment strategies differ greatly depending on injury pattern. In order to select an appropriate treatment strategy, one must accurately diagnose the injury pattern based on clinical examination and the use of appropriate imaging studies. The fundamental basis for diagnosis of a medial sided knee injury stems from understanding the static and dynamic stabilizing structures that compose the medial side of the knee. It is our aim to define the anatomic roles of medial sided structures, their importance in protecting the biomechanical stability of the knee, as well as provide indications and our preferred procedures for surgical management of these complex injuries.