Medial and posteromedial corner knee injuries are being increasingly recognized as a growing problem in the field of sports medicine. These injuries can cause medial knee pain and side-to-side instability with activity, particularly with participation in sports. Understanding the local anatomy and the native healing properties of the medial aspect of the knee is crucial for the successful treatment of these injuries. Proper diagnosis is best achieved through a combination of physical exam, objective valgus stress radiographs at both 0° and 30° of knee flexion, and magnetic resonance imaging. Management of medial-sided ligament knee injuries includes both conservative and operative treatment, with anatomic reconstruction demonstrating both biomechanical validation and favorable clinical outcomes. Failure to successfully restore medial knee laxity can lead to chronic instability, knee pain, and cruciate ligament failure. Despite the complexity of posteromedial corner injuries, relying on surgically relevant anatomical landmarks is key for successful surgical reconstruction.