Granted a commission as an ensign in the first regiment of the Grenadier Guards by the Duke of Gloucester in May 1800, Woodford finished his time training in Brunswick before his return to Great Britain to join his regiment in 1801. Upon his return, he was befriended by William Douglas, 4th Duke of Queensberry, who presented him with a fine horse and led him to the King at Windsor. This friendship proved fortunate, as Douglas left him £10,000 in 1810. Although Woodford joined the regiment in 1801, he did not see active service until 1807, when he was involved in the Battle of Copenhagen. Following this, in 1808, he was sent to the Peninsula under the command of Sir David Baird to join with the forces of Sir John Moore. Here, Woodford was appointed deputy-assistant quartermaster-general and aide-de-camp to Moore. Involved in the retreat to Corunna, it is said that Woodford's heel was injured by the last shot fired in the Battle of Corunna at dusk. As a result of this, Woodford was unfit for military service for eighteen months until he was able to join the Duke of Wellington's army, which had just crossed the Ebro. Woodford continued his previous roles and was a participant in numerous battles, including Nivelle, Nive, Orthez, and Toulouse.