The legend says that the most ancient settlement here was Coccheto, and that it was destroyed by a natural calamity. In roman times it was called Casale, since it was probably the country estate of some rich Roman family. After the fall of the Roman empire, it was included in the Lombard countdom of Benevento. Then the Normans occupied Molise, dividing it into the two counties of Loritello and Molise, and Casalciprano was included in the latter. In the Catalogum Baronum of the 11th century the center is still called only Casale, then in the following century the word "Ciprani" was added from the surname of some Ciprani lords. Under the Anjou Casale Cipranorum was ruled by the d'Evoli family who gave it in the 16th century to the Mazzacane, followed by the de Raho. In 1735 don Gaetano de Leto Duke of Polignano married Nicoletta de Raho of Casalciprano, and the De Leto family kept the fiefdom until 1805.
In the 19th century the political conditions and the economic crisis of the pastoral economy gave rise to brigandage, and the Matese and its forests were famed for the many powerful gangs that threatened the peaceful life of the population. The most famous brigands of Casalciprano were Costanzo Eugenio Lombardi, Pasquale Picciano, alias Rosciuolo, Gaetano Policella, and Gaetano Corsilli. Brigandage then disappeared, giving way to emigration to Europe and the Americas as an outlet to the economic and social difficulties of Southern Italy in the late 19th and early 20th century.