Chesterfield, of 180 tons (bm), first appeared in Lloyd's Register in 1791 with P. Oke, master, Thomas York, owner, and trade Halifax, Nova Scotia–Portsmouth.

[7] In April 1793 Lieutenant Governor Francis Grose chartered Chesterfield for £120 to take provisions and personnel to Norfolk Island.

The islanders attacked a party of seven men in two boats from the ships, killing four men, including Captain Hill, of the New South Wales Corps, and three lascars, when the sailors were discovered polluting Darnley Island's only supply of fresh water.

Captains Alt and Bampton next travelled to Stephens Island in search of a boat that had gone missing during the attack.

[10][11][12] The missing boat, containing the three survivors from the original party having drifted away from the ships, Mr. Shaw, Chesterfield's mate, sailed it towards Timor.

Lloyd's List reported on 28 February 1794 that Chesterfield, Alt, master, had arrived on 10 December 1793 at the Cape from Botany Bay.

[13] Captain Alt returned to England on 29 October 1794 with 54 tuns whale oil, 40 Cwt bone, and 300 seal skins.

[6] Lloyd's Register for 1799 showed Chesterfield's master changing from J. Nichol to N.Brooks, her owner from Jarret Jr to Williams, and her trade from London–South Seas to London–Cape of Good Hope.

[1] On 4 March 1805 Carpenter observed Chesterfield west of Gibraltar, heading east, and passed close by.

[17] The Spanish privateer Fuerte, of Cadiz, brought Chesterfield and Hannah, Horn, master, into Málaga in Spain on 6 March.