USS Welborn C. Wood became one of the first of the 50 over-age destroyers to be transferred to the British government in return for 99-year leases on important base sites in the Western Hemisphere. She and the rest of her division, Destroyer Division 67, arrived at Halifax, Nova Scotia, on 6 September 1940. Her crew instructed the Britishers slated to man the ship in the brief few days preceding the turnover ceremonies. On 9 September, Welborn C. Wood's commissioning pennant came down; her American crew mustered ashore and marched off to board a train waiting to take them back to the United States; and the British officers and ratings assigned to the "flush decker" manned the destroyer. Welborn C. Wood was subsequently struck from the Navy list on 8 January 1941.

Commissioned into the Royal Navy simultaneously, the destroyer became HMS Chesterfield (I.28). Initially, her new crew must have found the ship difficult to handle, as she twice rammed HMS Churchill (I.45) (formerly Haraden, DD-138) which was Iying alongside a pier, fitting out, before she sailed for the British Isles. As part of the first "Town" flotilla so called because each British ship bore the name of a town common to both Great Britain and the United States (the Canadian vessels six of them bore names of common rivers) Chesterfield sailed for Belfast, Northern Ireland, and arrived at her destination on 18 November. Shifting to Plymouth on the 22d, the destroyer underwent a refit at Chatham before joining the 11th Escort Group, Western Approaches Command, based at Greenock.

From 1941 to 1943, Chesterfield escorted convoys in the North Atlantic. Screening Convoy HX-222 on 17 January 1943, the destroyer attacked U-268 with a depth charge barrage, only to suffer damage from her own charges. Limping to Plymouth for repairs soon thereafter, the ship remained there until November 1943.

Allocated to the 5th Western Approaches Command for duty as a target vessel for aircraft, she remained engaged in this vital, but unglamorous, duty through 1944. Subsequently placed in reserve at Grangemouth Firth of Forth, on 17 January 1945 Chesterfield was eventually broken up for scrap in 1947.