Woodriff was commissioned as a lieutenant on 1 April 1783, and received promotion to the rank of commander on 18 September 1795, and to captain on 28 April 1802.
Voyage to Australia
Towards the end of 1802 Woodriff was appointed to command of the, a 50-gun ship armed en flûte, and fitted to transport convicts. They were bound for Port Phillip in the Bass Strait, on the southern extremity of Australia, with the intention of setting up a new settlement there under the command of David Collins. Calcutta sailed from Spithead on 28 April 1803, in company with the storeship Ocean, calling at Rio de Janeiro in July, and the Cape of Good Hope in August; they arrived at their intended destination in October. Calcutta then sailed alone to Port Jackson to take on a cargo of 800 tons of timber. Whilst in Sydney, Woodriff and the crew of Calcutta assisted in suppressing the Castle Hill convict rebellion. For this service Woodriff received a land grant near Penrith, New South Wales in 1804. Calcutta then before sailing back to England via Cape Horn and Rio de Janeiro, arriving back at Spithead on 23 July 1804, completing a circumnavigation in ten months and three days.
The Calcutta was refitted as a 50-gun ship, and sent to Saint Helena to escort merchant ships back to England. She arrived there on 3 August 1804 and sailed in company with six merchant ships back to England. Unfortunately, on 26 September, as the convoy approached the entrance to the English Channel, they encountered a powerful French squadron. Woodriff attacked, sacrificing his own ship in order to give the convoy a chance to escape, which all but one did, while the Calcutta was forced to surrender. Woodriff, his officers, and crew were landed at La Rochelle three months later, and marched to Verdun, away. In June 1807, Woodriff was released in a prisoner exchange, and promptly court-martialled for the loss of his ship. He was honourably acquitted, and his conduct was pronounced to have been that of "a brave, cool, and intrepid officer."
He was born on 17 December 1756, the son of John Woodriff of Deptford, Kent. He married Asia Sumarel ; they had three daughters, and three sons: Capt. RN, Cdr. RN, and Lt. Robert Mathews Woodriff RN.
