Patients with foot pain commonly present to their primary care physicians for their initial management and treatment. These patients and their respective foot or lesser toe pain can present the physician with a complex problem with a long differential list. Depending on the timing of the pain and underlying pathology, these differentials can be divided into acute and acute exacerbation of chronic conditions. This review categorizes the history, physical exam, radiological findings, conservative treatment, and surgical management for each major cause of lesser toe pain, whether acute or chronic. The acute conditions surrounding lesser toe pain in the adult population discussed are toe fractures, toe dislocations, and metatarsal head and neck fractures. The chronic pathologies surrounding lesser toe pain in the adult population evaluated in this review include metatarsalgia, Morton’s neuroma, Freiberg infraction, brachymetatarsia, bunionettes, and lesser toe disorders.