On the occasion of the sending of the Invincible Armada against England, the first procession of Our Lady of Regla was held. It was organized by the Duchess of Medina Sidonia, Ana Gómez Silva y Mendoza, who convinced the Prior of the Augustinian community to take the Virgin in procession to pray for the success of our Navy. It was September 8, 1588.
During the 16th and 17th centuries, the Image of Our Lady of Regla was, without a doubt, the best known and most popular in Andalusia.
The historians of that time number eighty thousand people who took part in that great religious demonstration. The chronicler from Chipiona, Fray Diego Carmona Bohórquez, in his book “Historia Sacra” gives us extensive and detailed descriptions of the processional procession and the extensive retinue, made up of most of the Spanish nobility of the time.
They say that the first banners had already reached Sanlúcar de Barrameda, which is 9 kilometers from Chipiona as we all know, and the Image of the Blessed Virgin had not yet left here, from its church in Regla.
From the beginning of the 17th century, the custom of carrying the Image of Our Lady of Regla in procession around the Sanctuary on the day of her feast, September 8, was introduced, overflowing with this reason the towns and cities of Andalusia, which in number of about thirty thousand, came to venerate their loving Mother, to receive the sacraments, and to attend solemn Mass.
At that time, everything that belonged to Our Lady of Regla was held in great appreciation and esteem and was considered as a pledge of affection and deep veneration: the measurements of her Image, the tile on which she was seated, the key to the Granada dungeon. , the oil of his lamp, the coins of the poor devotee, the leaves of his fig tree, everything that had belonged or touched the Image. 

News from https://www.chipiona.city/news/index.php/cultura/46-historia/702-primera-salida-en-procesion-de-la-virgen-de-regla-de-chipiona