The expedition along with the blockade took place between May and July 1591 led by Ralph Lane and Michael Geare with a large financial investment from John Watts and Sir Walter Raleigh.

[3] The first and main fleet was financed largely by John Watts, but also had investment from Walter Raleigh, Paul Bayning, and Sir Francis Drake.

[15] The expedition's first success came in late May when a 150-ton Spanish merchantman Rosario of Master Francisco González was captured by Marageret and Prudence near La Yaguana off Hispaniola.

The prisoners informed the English that a Spanish fleet of seven galleons, two galleys, and two pinnaces with 2,000 men in total were destined to arrive in the area of Western Cuba.

He had left Havana in early June to sweep any English privateers from the designated area as this was in anticipation of a plate fleet led by Antonio Navarro de Prado.

[6] The Spanish galleys, unable to make an impression and suffering considerable damage then stood off and rejoined de la Ribera's galleons.

[15] On 29 June Hopewell and Swallow returned to Cape Corrientes to find no sign of any Spanish ships under de la Ribera.

[6] The English sailed towards her, attacked the ship, and after heavy hand-to-hand combat and a number of casualties, they boarded and overwhelmed the Spaniard forcing its surrender.

[10] On the same day more success came to the English as Swallow, Centaur, Hopewell, and Fifth Part pursued four Spanish coastal ships which were surrounded and captured.

[10] The Santa Trinidad prize proved so rich that Lane immediately ordered the English to quit their watch outside Havana and protect the ship at all costs.

[6] In all Watt's expedition was a huge success – eight prizes were taken in all worth a total of £40,000 which produced on investment of at least 200 per cent regardless of embezzlement and pillage which crew members committed to supplement their normal one third share granted in lieu of wages.

[7] Watt's had taken most of the prizes and the money, and Carew who funded a small part asked Sir Julius Caesar to intervene on a matter of fair distribution.

[5] The Spanish Governor of Cuba Juan de Tejeda complained bitterly particularly as the English had sent him letters and compliments during the blockade:[5] for every hour they sail under my nose; in future I would like to be prepared that the enemy may not so insult me without my being able to get at him.

[5] Although they didn't repeat the huge success of the previous year's expedition, their operations forced the Spanish to delay the departure of two Treasure fleets.