The first wooden bridge across the Fontanka River along the axis of the modern Moskovsky Prospekt was built in 1717. In the middle, the bridge had a transverse gap 70 cm wide, intended for the passage of masted vessels; during the day, this gap was covered with boards. In 1738, the crossing was rebuilt.

Until 1738, the bridge had no official name. The popular name—Obukhov or Obukhovsky—became attached to it after the surname of the “posadsky man” Obukhov who built it. In 1738, the Commission on the Construction of Saint Petersburg assigned the name “Saarsky Bridge” to it. This name did not catch on, and the bridge still preserves in its name the memory of the contractor of the construction works—Obukhov.

During the construction of the granite embankment walls of the Fontanka in 1785–1786, the wooden bridge was rebuilt into a three-span stone bridge modeled after the tower bridges of Lomonosov and Staro-Kalinkin. The shore spans were covered with stone vaults, and the central span was a drawbridge with a wooden superstructure and towers on river piers to house the drawbridge mechanisms.

In 1865, the bridge was rebuilt according to the project of engineer Mikhailov. The wooden drawbridge superstructure was replaced by a brick vault, and the over-bridge towers were dismantled. Structurally, the bridge was transformed into a three-span rigid arch.

The Obukhovsky Bridge gave its name to the Obukhovskaya Predmostnaya Square on the right bank of the Fontanka River. Here is located the Petersburg State Transport University of Emperor Alexander I. Opposite the university entrance stands a monument to the founder of this educational institution, the outstanding Russian statesman, scientist, engineer, and architect of Spanish origin—Agustín de Betancourt.

The bridge spanning the Fontanka River along the axis of Moskovsky Prospekt connects Spassky and Bezymyanny Islands. It is a three-span stone structure 68.8 meters long and 31.8 meters wide. The bridge is skewed in plan, with a skew angle of 60°.

The superstructure consists of reinforced concrete two-hinged arches faced with granite. Structurally, these are reinforced concrete solid vaults. The abutments and piers are massive, on pile foundations, and faced with granite. The facades of the bridge express the outlines of the arches and feature profiled icebreakers shaped as triangular prisms.

The railing is made as a solid granite parapet. Granite obelisks rise at the entrances, each topped with two round-shaped lanterns. The sidewalks are separated from the roadway by a raised granite parapet-type railing.

By the mid-1930s, the bridge could no longer handle the increased traffic flow on International Prospekt (the name of Moskovsky Prospekt from 1918 to 1950): the bridge width was about 16 meters, while the avenue was 30.6 meters wide. Additionally, subsidence with joint openings up to 25 mm was detected in the brick vaults of the central span. In 1939, according to the project of engineer V.V. Demchenko and architect L.A. Noskov, the bridge was rebuilt into a three-span reinforced concrete structure.

On September 7, 1950, a gas pipeline laid with poor-quality welded seams caused a gas leak; an explosive mixture formed in the sidewalk on the upstream side, which detonated from a stray spark, damaging the reinforced concrete sidewalk slabs. After this incident, a decision was made to shut off gas pipelines on other city bridges—Novo-Petergofsky, Komsomolsky, and others.

In 1962, tram rails were removed from Moskovsky Prospekt on the section from Mira Square to the Obvodny Canal.

In 1968, the spheres crowning the obelisk-torchères were re-covered with gold leaf.

In 1989, the sidewalks were separated from the roadway by a granite parapet.

In 2014, the artistic and architectural lighting of the Obukhovsky Bridge was reconstructed.