Osteochondral lesions of the elbow are injuries that disrupt the cartilage and subjacent bone, and they most commonly involve the capitellum. The staging, prognosis, and treatment of osteochondral lesions in the elbow are based on a combination of radiographic, magnetic resonance imaging, and arthroscopic findings. Radiographic staging includes the radiolucent, separation, and free (advanced) stages. MR imaging features of instability include cysts, osteochondral fracture, T2 hyperintense rim, subchondral plate defects, and fluid-filled osteochondral defects. Finally, arthroscopic grading of osteochondral lesions increases in severity based on findings of softened cartilage, cartilage fissuring, exposed bone, loose but nondisplaced fragments, and eventually displaced fragments resulting in intra-articular bodies. This pictorial review focuses on osteochondral lesions in the capitellum and trochlea including osteochondritis dissecans, Panner disease, and acute trauma.