HMS Chesterfield was a 44-gun fifth-rate ship of the Royal Navy which saw active service in both the War of the Austrian Succession and the Seven Years' War. Built to an antiquated design, she was commissioned into service in 1745 and assigned to the Navy's Western Squadron guarding the English Channel and the nearby waters to protect merchant vessels en route to English ports. In 1747 she secured her first victory at sea with the capture of a 10-gun Spanish privateer.

In the following year Chesterfield sailed to West Africa to make an annual survey of British forts. A mutiny during this voyage led to the stranding of her captain on shore and an attempt by the first lieutenant to take the ship to the West Indies to steal supplies. Retaken by loyalists among the crew, Chesterfield was surrendered to British authorities in Antigua in December 1748. A subsequent court martial led to the execution of two officers and five others on board.

Chesterfield was decommissioned in 1748 but restored to active service in 1755 as Britain rearmed for the Seven Years' War with France. Present but not directly engaged in the Battle of Minorca in 1756, she was instrumental in transporting British wounded to Gibraltar for care. Later service included voyages between England and North America to protect British convoy vessels, as well as patrols of American coastal waters. In 1758 she captured two brigantines on the York River in Virginia, which were later found to be trading with the enemy. For the remainder of the Seven Years' War she was principally assigned to convoy escort duties between England and North America, other than one brief return to West Africa in 1760 during which she fought off an assault by pirates. After 16 years of service, she was wrecked off northern Cuba in July 1762 while escorting troop transports to assist in Britain's Siege of Havana.

Chesterfield was an oak-built 44-gun fifth-rate, one of 16 vessels constructed according to the 1741 revisions to the 1719 Establishment which set specific requirements for scantlings, materials, fitting and armament for Royal Navy craft. Principles underpinning the 1719 Establishment were drawn from Admiralty observation and practice from the mid-seventeenth century, with minor modifications in the subsequent revisions. For Chesterfield the 1741 revisions allowed minor increases in length, beam and depth of hold, and the addition of four 6-pounder guns at the rear of the quarterdeck. These changes aside, Chesterfield was built to a design largely unchanged from that of fifth-rate Royal Navy ships from the previous century. Notably, no allowance was made for the use of longer, sleeker hulls such as were becoming common in equivalent French vessels by the 1740s.

Orders for Chesterfield were issued during the middle years of the War of Jenkins' Ear, when Britain's Royal Dockyards were fully engaged in building and fitting-out ships of the line. Consequently, and despite some Navy Board misgivings, contracts for small and mid-sized vessels were issued to private shipyards, with an emphasis on rapid completion. Chesterfield's contract was therefore signed on 23 May 1744 with private shipwright John Quallett of Rotherhithe in South London. Work was to be finished within one year for a 44-gun vessel measuring approximately 705 tons burthen, for a fee of £7,554 paid through periodic imprests drawn against the Navy Board. In practice neither the timeline nor the budget were met. Chesterfield's keel was laid down on 2 June 1744 but construction lasted seventeen months with the ship not ready for launch until 31 October 1745. The final cost was £7,931, with an additional £5,097 set aside for fitting out.

The vessel was named after Chesterfield, a market town in Derbyshire, England. This continued a Board of Admiralty tradition dating to 1644, of naming ships for geographic features. Overall nine of the 16 vessels in the 1741 Establishment were named after well-known regions, castles or towns.

As built, Chesterfield was 127 ft 5 in (38.8 m) long with a 102 ft 8 in (31.3 m) keel, a beam of 36 ft 3.5 in (11.062 m), and a hold depth of 15 ft 5 in (4.7 m). At 719 38⁄94 tons burthen, she was the second largest vessel in the 1741 Establishment after HMS Ludlow Castle, and a full fourteen tons over the stipulated contract size. Her armament comprised 20 nine-pounder cannons on her upper deck, and 20 eighteen-pounder cannons on the enclosed lower deck close to the waterline. These broadside weapons were supported by four six-pounder guns at the rear of the quarterdeck behind the wheel. The Admiralty-designated complement was 280 comprising four commissioned officers – a captain and three lieutenants – overseeing 59 warrant and petty officers, 133 naval ratings, 45 Marines and 39 servants and other ranks. Among these other ranks were six positions reserved for widow's men: fictitious crew members whose pay was retained by the captain to be reallocated to the families of sailors who died at sea.

The concept of 40- and 44-gun fifth rate ships such as Chesterfield had been developed in the seventeenth century when the Royal Navy was principally deployed in short-range operations in the English Channel and adjacent waters. Chesterfield was one of the last to be constructed before Admiral Anson's 1751 reforms introduced a new class of 74-gun vessels as the minimum size for a ship of the line and promoted development of small fast frigates of around 32 guns to chase the enemy close to shore. Under these reforms a 44-gun fifth-rate such as Chesterfield became an anachronism: too small to be effective in the line of battle and too slow to pursue opposing frigates or privateers. Instead, the impetus for Chesterfield's construction was Admiralty's realisation that too few middle-sized vessels were available to protect merchant convoys and conduct routine patrols in the Channel, the Mediterranean and off the coast of Africa. Many existing fifth-rate vessels were also derelict: of the nineteen listed as being in service in 1739 only seven were seaworthy with another five salvageable after major repairs. The dearth of convoy escorts was so severe that in 1741 Admiral Thomas Mathews complained that he was using 70-gun ships of the line simply to guard Mediterranean trade. Vessels such as Chesterfield were urgently needed to alleviate this shortfall and allow larger vessels to resume other roles.