Peroneal tendon pathology is becoming an increasingly recognized source of lateral-sided ankle pain. High clinical suspicion, along with judicious physical examination coupled with confirmatory advanced imaging modalities, are necessary to make an accurate diagnosis and aid in guiding treatment. Peroneal pathology encompasses several distinct conditions. Peroneal tendon tears and injuries to the peroneal retinaculum must be identified to guide treatment. Patients with peroneal pathology report high levels of satisfaction after surgical management with most returning to their preinjury level of function. An early and accurate diagnosis, along with treatment tailored to the individual, is necessary to obtain optimal outcomes.