The regiment was raised as the 20th (Jamaica) Regiment of (Light) Dragoons in 1792;[1] it was deployed to Jamaica in 1795 during the Second Maroon War.

[2] The regiment saw action at the Battle of Blaauwberg in January 1806 during the second invasion of the Cape Colony,[3] and later at the Battle of Montevideo in February 1807 during the British invasions of the River Plate.

[4] The 3rd Squadron was the sole cavalry detachment present in the Alexandria expedition later that year.

[5] It also fought at the Battle of Rolica and at the Battle of Vimeiro in August 1808 during the Peninsular War.

[1] In 1805 its title was simplified again to the 20th Regiment of (Light) Dragoons; it was disbanded in 1818.