Born in Aquasco, Prince George's County, in what was then the British Province of Maryland, Leonard Covington joined the United States Army as a cornet in March 1792.

He was promoted to captain in 1794 and served in the Northwest Indian War (1785–1795) under Anthony Wayne, where he distinguished himself at Fort Recovery and the Battle of Fallen Timbers.

In 1809, Leonard Covington returned to the Army as colonel of light dragoons, having served many years in the Maryland House of Delegates and in 1805–1807 as a Representative (Democratic-Republican Party) in the Ninth Congress.

Covington was mortally wounded in the Battle of Crysler's Farm and died three days later at French Mills, Franklin County, New York.

[5] Mrs. Leonard Covington was the former Rebecca Mackall, his first cousin and a relative of the family of General James Wilkinson.