Born at 30 Welbeck Street, London, the son of Lieutenant-Colonel John Woodford and Lady Susan Gordon (daughter of Cosmo Gordon, 3rd Duke of Gordon), Woodford was educated at Winchester College and Royal Military Academy, Woolwich before being commissioned as an ensign in the 9th (East Norfolk) Regiment of Foot on 6 December 1794. He was promoted to lieutenant in the 22nd (the Cheshire) Regiment of Foot on 15 July 1795 and transferred back to the 9th (East Norfolk) Regiment of Foot in September 1799 before seeing action at the Battle of Alkmaar in October 1799 (where he was wounded) during the Anglo-Russian invasion of Holland. Promoted to captain lieutenant on 14 December 1799, he transferred to the Coldstream Guards on 28 December 1799 and became aide-de-camp to Major-General Sir James Forbes in Sicily in 1803. He took part in the Battle of Copenhagen in August 1807 before rejoining Lord Forbes' staff in Sicily in March 1808. After returning London, he was promoted to lieutenant colonel on 8 March 1810.