Diseases of the peroneal tendons and superior peroneal retinaculum (SPR) are frequently underdiagnosed causes of lateral ankle pain and instability. Common diseases include tenosynovitis, rupture, and dislocation of the peroneal tendons as well as injuries to the SPR. Many anatomic variants, such as a flat or convex retromalleolar fibular groove, hypertrophy of the peroneal tubercle, an accessory peroneus quartus muscle, a low-lying peroneus brevis muscle belly, or an os peroneum, may be associated with or predispose to lateral ankle disease. Magnetic resonance (MR) imaging is excellent for detecting soft-tissue and bone variants and abnormalities related to the lateral ankle. Knowledge of the MR imaging appearances of these entities aids radiologists in making the precise diagnosis of disorders of the peroneal tendons and SPR. Pitfalls and normal variants of the peroneal tendons, including magic angle phenomenon, pseudosubluxation of the peroneus brevis tendon, a bifurcated or mildly crescentic peroneus brevis tendon, insertion of the peroneus quartus tendon into the peroneus brevis tendon, and the presence of an os peroneum are important to recognize. It is also useful to be familiar with the MR imaging appearances of SPR injuries, which can be an overlooked but treatable cause of lateral ankle pain and instability.