Tarsal coalitions are relatively rare diagnoses affecting adolescent patients that typically present with progressive foot pain. Cuboid-navicular coalition, a type of tarsal coalition, is extremely rare with less than 10 reported cases to date. Most prevailing theories reported have described this specific type of coalition as asymptomatic except at specific moments of stress and exercise. The purpose in presenting this case is to demonstrate that cuboid-navicular coalition can be associated with chronic unremitting pain, as in our patient. We present a case of cuboid-navicular fibrocartilaginous coalition in an adolescent patient presenting with chronic foot pain. Furthermore, from an imaging standpoint, radiographic findings are often subtle and radiologists cannot rely on indirect signs such as talar beak in clinching the diagnosis of cuboid-navicular coalition. Instead, abnormal articulation between the cuboid and navicular must be sought.