Second in command was Middleton's brother John, a company captain who secured Henry as a mercantile agent with a berth on the voyage.
[1] Middleton was sent onwards to Priaman on the west coast where he procured substantial quantities of pepper and cloves before returning home safely in the summer of 1603.
[2] They would encounter severe Dutch East India Company hostility, which saw the beginning of Anglo-Dutch competition for access to spices.
With the Red Dragon now under the command of Middleton,[4] the fleet departed Gravesend on 25 March 1604 but were delayed at the Downs as they did not have the correct complement of men.
[7] On 24 April, 570 kilometres off the coast of Western Africa, they anchored at Maio, Cape Verde and went ashore in search of fresh food and water.
[11] Having landed at Table Bay, the company traded successfully with the local inhabitants, securing over two hundred sheep and a number of "beeves".
[15] Following attacks from the native population, the fleet's company returned to their ships on 14 August, and then, with fair winds, set sail five days later.
It was decided that the Hector and Susan would return to England with their cargoes of pepper[17] and the Red Dragon and Ascension would proceed eastwards to acquire cloves and nutmeg.
[20] In view of this, Middleton decided to split up the two vessels, with the Red Dragon sailing to the Moluccas for cloves and the Ascension making for the isles of Banda to acquire nutmeg and mace.
[23] Middleton attempted to persuade the Ternatans to allow a trade monopoly and the establishment of an English factory but he lacked the authority needed to pledge the required protection from both Portuguese and Dutch aggression.
[1] Middleton arrived at Tidore on 27 March, and the following day met Thomè de Torres, captain of one of the Portuguese galleon.
That evening Captain de Torres came aboard and told Middleton that they (the Portuguese) were sure of victory against the Dutch, and would trade any remaining cloves with the English.
The morning of 9 May, the attack began before sunrise, and catching the Portuguese unaware, the Dutch and Ternate scaled the walls and raised their colours in the fort.
As commander Middleton went ashore at Mocha and was greeted with great pomp by the Agha, but a week later the English were attacked and robbed by their hosts.
He escaped but found in Surat the company's representatives had been forced to abandon trading due to Portuguese pressure on the local authorities.