The superficial medial collateral ligament (sMCL), deep medial collateral ligament (dMCL), and posterior oblique ligament (POL) are the three most important static stabilizers of the posteromedial corner (PMC) of the knee. Historically, the lateral side of the knee has been considered the “dark side of the knee” due to its complexity and the unknowns that come with it. Considerably less is reported about the medial side of the knee, specifically the complex anatomy and biomechanics of the PMC. Medial knee injuries are oftentimes misdiagnosed as simply medial collateral ligament (MCL) injuries and are left to heal on their own, leading to significant and chronic functional limitations in a subset of patients. A thorough physical examination supplemented with valgus stress radiographs and magnetic resonance imaging (MRI) is imperative to making an accurate diagnosis. Grade-I and II injuries to the sMCL typically do not require surgical intervention; however, grade-III injuries commonly do, and their treatment algorithm depends heavily on reliable identification of any concomitant ligament injuries. Recent studies have improved the understanding of this daunting region of the knee and have led to the development of anatomic-based reconstruction techniques to improve patient outcomes beyond that of repair or nonanatomic reconstruction.