On 13 Jun 1596 Robert Devereux 2nd Earl Essex (age 30) departed from Plymouth, Devon [Map] with a fleet of 150 English and Dutch ships divided into four squads with 6,360 private soldiers, 1,000 English volunteers, and 6,772 sailors.

Charles Howard 1st Earl Nottingham (age 60) was admiral in command. Robert Devereux 2nd Earl Essex (age 30) commanded the land forces. Edward Conway 1st Viscount Conway (age 32) commanded a foot Regiment.

Thomas Howard 1st Earl Suffolk (age 34), Walter Raleigh (age 42), Francis de Vere (age 35) each commanded a squadron.

Anthony Ashley 1st Baronet (age 35) represented Queen Elizabeth (age 62).

Toby Caulfeild 1st Baron Caulfeild (age 30) was present.

On 27 Jun 1596 William Hervey 1st Baron Hervey (age 31) was knighted at Cádiz by Robert Devereux 2nd Earl Essex (age 30) at the Sack of Cádiz.

On 29 Jun 1596 the fleet arrived in Cádiz Spain. In the Bay of Cádiz some 40 Spanish ships, ranging from galleys to galleons, as well as 16 other vessels from the Spanish convoy, which were disarmed and ready to depart for the West Indies. These unarmed vessels immediately fled to Puerto Real for refuge.

On 30 Jun 1596 at two in the morning the Anglo-Dutch fleet could be seen from Cádiz Spain, but it could not enter the bay due to bad weather. At five o'clock in the morning, both sides commenced an intense artillery barrage. After two hours, the Spanish fleet, outnumbered by the English, had to retreat to the interior of the bay. In the fray, the Spanish galleons San Andrés and San Mateo were captured, while the San Felipe and Santo Tomás sank, set fire by their captains in the face of possible capture by the Anglo-Dutch forces. They entered the bay at eight o'clock in the morning.

On 14 Jul 1596 the English burned Cádiz and the next day they left the bay, taking the hostages with them since the Spanish authorities had not been able to pay the ransom. The sacking of Cádiz in 1596 was one of the worst Spanish defeats in the course of the war, together with the attack on Cádiz of 1587 and the loss of the Armada in 1588. The economic losses produced by the Earl of Essex's expedition against the city and the anchored fleet in the port, estimated at 5 million ducats,contributed to the bankruptcy of the royal treasury that same year. The city of Cádiz remained devastated; in addition to the churches and hospitals, 290 out of a total of 1,303 houses burned.

Robert Radclyffe 5th Earl of Sussex (age 23) was knighted by Robert Devereux 2nd Earl Essex (age 30) for the taking of Cadiz.

Governor Thomas Gates was knighted by Robert Devereux 2nd Earl Essex (age 30) for his bravery.