[citation needed] King Manuel wished to become involved in the Indian Ocean trade network, expecting to derive great profits from importing spices to Europe via the Cape Route, bypassing the numerous middle-men that traded in valuable merchandise through the Red Sea, Egypt and the Middle East, where they were acquired by Venetian merchants and sold in Europe.

[citation needed] The existence of the wealthy trade hub of Malacca was known to King Manuel of Portugal since at least 1505, from second-hand information collected by captains in India.

[citation needed] Diogo Lopes de Sequeira successfully reached the city and was warmly welcomed by the local sultan Mahmud Shah, who granted the Portuguese commander authorization to establish a feitoria or trade post.

[citation needed] Albuquerque subsequently led an expedition of 16 ships, 700 Portuguese soldiers and 300 Malabarese auxiliaries that succeeded in wresting the city from the unpopular Sultan Mahmud, with the support of part of its population, after a military operation that lasted two months from July 1 to September 1.

[13] Due to a lack of familiarity of the geography of the region, particularly its shallow waters, the Portuguese withdrew after losing 20 men and one light oarship.

[17] The captain of Malacca Jorge de Albuquerque detached a flottilla to face the Malays within the river and disperse them in April, however a heavy storm scattered the ships of the Portuguese, and three were ambushed with 65 soldiers being killed upon entering into Muar.

[citation needed] In June 1524, Martim Afonso de Sousa destroyed 36 junks at anchor at Patani, which had allied with Pahang and Bintan, and torched the city, including the surrounding dusun cropfields, orchards and palm groves.

[21] Taking advantage of the unusually large numbers of soldiers available in Malacca, captain Dom Pedro Mascarenhas decided to undertake a vigorous campaign on Bintan and neutralize Sultan Mahmud once and for all.

[22] With 15 ships, 600 Portuguese soldiers, 300 Malay auxiliaries and an unrecorded number of sailors and combat-slaves, Dom Pedro blockaded the island-kingdom of Bintan and laid siege to its capital city.

In 1533 the Sultan of Johor had a Portuguese ambassador publicly tortured to death with boiling water, which amounted to a declaration of war.

[25] After the death of his brother Paulo, the captain of Malacca Estevão da Gama attacked Johor on June 1535, with a carrack, a square-rigged caravel and 18 light oarvessels with about 400 Portuguese soldiers plus 400 "combat slaves".

[26] The Portuguese sailed up the river which led to Johor and engaged its defenses but the Sultan fled to the jungle under the cover of the night.

[27] The Sultan witnessed the battle from atop an elephant, and again attempted to evacuate into the jungle, but he suffered a revolt and his baggage train carrying his treasure was assaulted mid-retreat by his own fleeing forces.

[29] In 1576, the Sultanate of Johor was attacked by Portuguese forces led by Antão de Noronha, aiming to strengthen their influence in the Strait of Malacca.

[31] A large Johor fleet attempted to attack Malacca itself, but was driven back by the presence of heavily armed galleons in its harbour.

[33] The Portuguese captured ample spoils, which included over 1,000 cannon, the great majority of them of small caliber, 1,500 firearms, and burned upwards of 2,000 craft of many sizes.

Upon spotting the Portuguese, the Sultan of Johor panicked, set his capital on fire and fled into the jungle, along with the resident Dutch merchants.

[citation needed] After years of intermittent conflict, the Dutch East India Company had amassed a force of 2,000 Europeans at Batavia by August 1639, with the intent of sending the troops to Malacca.

The previous commander, Cornelis Symonz van der Veer, had died since then, so Sergeant Major Adriaen Antonisz was sent in his place.

The Portuguese garrison consisted of 260 men, although the Dutch claimed that the best soldiers in the defence were the native and mixed-racial inhabitants, who numbered about 2,000–3,000 in total.

[38] After an over five-month siege, Malacca was seized by the Dutch East India Company, ending nearly 130 years of official Portuguese presence in the region.