In the Middle Ages, this ravine was one of the most important routes of entry into Madrid and connected the town with the old road to Segovia, which started on the other side of the Manzanares River.

The Bridge of Segovia (1582-1584) succeeded in crossing the Manzanares, attributed to the architect Juan de Herrera, which replaced the original, built in the first half of the fourteenth century by Alfonso XI of Castile.

Abundant in fresh water, the area in the wash of the basin of San Pedro enjoyed many orchards and was called El Pozacho, which was named after a waterwheel or similar hydraulic device which may have existed there.

Bailén Street ended abruptly at the edge of this ravine, forcing pedestrians to make the difficult descent and ascent to reach the area of the Royal Alcázar of Madrid.

This conceptualization required an extension of Bailén Street crossing above and bridging the gap perpendicularly over this ravine, thus joining the Royal Palace area with Vistillas to the south and beyond.

Some houses and establishments were demolished, including the original cathedral of Madrid, in order to level the field, creating a gateway to the city.

This idea of a viaduct for urban design motivation was proposed again by the royal architect Silvestre Perez during the reign of Joseph Bonaparte (1808-1813).

This involved the expropriation and demolition of several residential and religious buildings, including what was considered the oldest church in Madrid, the Santa Maria de la Almudena, in 1868.

The bridge was originally built in 1874 by the city engineer Eugene Barron Avignon, within the overall reform project based on Bailen Street, involving the creation of a large avenue, oriented nearly north-south, uniting two monuments, the Royal Palace and the San Francisco el Grande Basilica.

In 1931, The poor condition of the old viaduct caused the government of the Second Republic to hold a competition to design the current one; the contest was canceled by the College of Architects and reconvened the following year.

The viaduct was damaged significantly by artillery in the Siege of Madrid during the Spanish Civil War, due to its proximity to the front lines.

In October 1998, under the term of José María Álvarez del Manzano, the City of Madrid installed thick acrylic glass barriers to keep people from jumping off, partially due to the danger it was posing to pedestrian and vehicular traffic below.

It features frequently in the literary-bohemian world of Madrid in works by authors such as Valle-Inclán (Bohemian Lights), and Benito Pérez Galdós.