The medial collateral ligament (MCL) is the most commonly injured knee ligament. Most will heal well with nonoperative treatment. However, not all medial knee injuries are the same. A detailed physical examination can help determine the severity of the medial-sided injury. When combined with advanced imaging, the examination will delineate damage to associated medial knee structures, including the location of MCL damage, posteromedial capsule injuries, and combined cruciate injuries. Failure to recognize MCL injuries that may be prone to chronic laxity can lead to significant disability, joint damage, and failure of concomitant cruciate ligament reconstructions. Magnetic resonance imaging is the mainstay of diagnostic imaging, with coronal sequences allowing full assessment of the MCL complex. Tangential views aid in the diagnosis of concomitant injuries. Stress radiography can play a role in evaluating MCL healing and subtle chronic laxity. Ultrasonography is also gaining acceptance as a means to assess MCL injuries. Use of a detailed examination and advanced imaging will allow optimal treatment of medial knee injuries and improve clinical outcomes.