According to legend the statue of Our Lady of Regla was commissioned by Augustine of Hippo (354 - 430) and brought to Spain by Cyprian the Deacon after Augustine's death and the Vandal invasion of North Africa. It was enshrined in the seaport city of Chipiona where it was venerated both by Augustinian canons and African hermits.

Following the 8th-century invasion of Andalusia by the Saracens, the monks hid the statue in a cistern next to a fig tree where it remained until after the liberation of the country by Alphonse X of Castile (1221-1284), when the Virgin appeared to a canon regular from León directing him to the hiding place. The rediscovery of the hidden image, along with a chalice and a miraculously still-burning lamp, led to the revival of the devotion. The cistern and fig tree still exist and the location is called Humilladero. According to some scources, the name Regla is a reference to the Rule (regla) of the Augustinians.

The present statue is thought to date to c.1200 and is believed to have always been a black Madonna rather than to have blackened with age and exposure to candle smoke. Unusually for a black Madonna, she holds a white Christ Child (not obvious in this image). The documented cult and earliest recorded miracles date from 1330 and the official act of the foundation of the monastery where she is enshrined is dated August 22nd, 1399, when the Count of Arcos, Don Pedro Ponce de León, entrusted the new foundation to the Order of Saint Augustine. The heydey of pilgrimage to Our Lady of Regla was in the late 18th century, especially following the shrine's miraculous survival of a devastating earthquake and tidal wave in 1755. This print dates from that period and was probably made for sale to pilgrims as a souvenir.