Majapahit
Decline

Following Hayam Wuruk's death in 1389, Majapahit power entered a period of decline with conflict over succession. Hayam Wuruk was succeeded by the crown princess Kusumawardhani, who married a relative, Prince Wikramawardhana. Hayam Wuruk also had a son from his previous marriage, the crown prince Wirabhumi, who also claimed the throne.

By the time of Hayam Wuruk's death, Majapahit had lost its grip on its vassal states on the northern coasts of Sumatra and the Malay Peninsula, the latter which according to Chinese sources, would become a tributary state of the Ayutthaya Kingdom until the rise of Malacca Sultanate, supported by the Ming dynasty.

In the 14th century a Malay Kingdom of Singapura was established, and it promptly attracted a Majapahit navy that regarded it as Tumasik, a rebellious colony. Singapura was finally sacked by Majapahit in 1398, after approximately 1 month long siege by 300 jong and 200,000 men. The last king, Parameswara, fled to the west coast of the Malay Peninsula to establish the Melaka Sultanate in 1400.
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