Siege of Johor
1587 CE.
Shown on the map at 1.487°, 103.781°.
The siege of Johor of 1587 was a military operation in which Portuguese forces successfully sieged, sacked, and razed Johor, capital of its eponymous sultanate. The city would later be rebuilt at a different location. In 1586 naval forces of Johor began diverting shipping to the Singapore Strait due to a lack of personnel available in Malacca. Malacca itself was threatened by a large Johor fleet, but it was driven back by the presence of heavily armed Portuguese galleons in its harbour.
Text from the Wikipedia article Siege of Johor (1587), licensed CC BY-SA 4.0.