The 1st Squadron was the 58th Infantry Brigade's reconnaissance unit and was deployed to Bosnia as part of Stabilization Force and to Iraq during Operation Iraqi Freedom.

The 1st Squadron, 158th Cavalry traced its lineage back to the organization of the Governor's Guard, an independent infantry company, at Annapolis on 17 August 1877.

The company was mustered into Federal service at Pimlico on 17 May 1898 for the Spanish–American War as a unit of the 1st Maryland Volunteer Infantry.

It was mustered into Federal service on 28 June 1916 at Camp Laurel to serve on the Mexico–United States border, replacing Regular Army units participating in the Pancho Villa Expedition.

The company was sent to the front in mid-1918 and fought in combat in Alsace and the Meuse-Argonne Offensive before being demobilized after the end of the war at Camp Meade on 2 June 1919.

It was inducted into Federal service on 3 February at Annapolis, serving with the 115th and the 29th Division in World War II.

After being sent to England, the company participated in the Normandy landings at Omaha Beach in June and advanced east through France and Germany until the end of the war in May 1945.

It was constituted on 1 March 1959 as the 29th Aviation Company (part) and organized and Federally recognized on 7 July 1959 at Baltimore before being relocated to Edgewood on 1 May 1960.

In September 2005, the UH-1-equipped squadron provided support and security to New Orleans residents in the aftermath of Hurricane Katrina.

In April 2007, the squadron was mobilized to deploy to Iraq in support of Operation Iraqi Freedom.

Its last commander was Lieutenant Colonel Michael Duplechain, and most of its 329 personnel were reassigned to other units in the Maryland Army National Guard.