Parameswara was a prince of Palembang. In 1930 he married a daughter of the Majapahit Emperor and became a vassal of the his father-in-law. Not long after he threw off his allegiance to the Majapahit Emperor, who at once sent warriors to drive him out of Sumatra. Parameswara fled to Tumasek, which was actually old Singapore with his family and followers. During this time Singapore was ruled by a Malay chief from Patani, who was appointed by the ruler of Siam. The Malay Governor treated Parameswara well, but Parameswara killed the Governor a few days later and made himself Chief of Singapore and the neighboring islands. Parameswara ruled Singapore for about five years as a sort of pirate captain.
During the middle of the 14th century, the Siamese who were expanding their territorial power in the north of the Malay Peninsula as far as the state of Pahang, failed to extend their powers to Singapore although attempts were made to attack Singapore. This was because the kingdom of Majapahit at that time was at the peak of its strength and power and was feared by other kingdom in the Malay Archipelago. Several states along the Straits of Melaka including Tumasik or Singapore, as it is now known were under the control of Majapahit. A Javanese fleet from Majapahit attacked Singapore during Parameswara?s reign of Singapore. After defeating Singapore, the Javanese returned to Java. Owing to this, it was believed that the attack made by the Javanese from Majapahit on Singapore did not result in the downfall of the kingdom of Singapore and Parameswara?s flight from Singapore but had however, continued to rule it in its declining condition.
When Parameswara failed to establish a kingdom at two places in Muar, that is, Biawak Busuk and Kota Buruk, he led his followers to a place known as Sening Ujung or now known as Sungei Ujong. He continued his journey from here until he came to the mouth of the Bertam River where he founded Melaka and became the first ruler around the year 1394. However, during this time, Parameswara was still a Hindu. Hence a Malay kingdom was therefore established in Melaka to continue the existence of the Malay kingdom of Singapore which had fallen.
After Melaka was founded, Parameswara began to develop the place and ordered his men to cultivate the lands with banana, sugar cane, yam and other crops for food. Parameswara himself carried on trade in Melaka. Within a short period of time, news about the town of Melaka begun to spread all over Malaya, Sumatra, Java and India which resulted in a large number of traders coming to trade in Melaka. Two years after Parameswara founded Melaka, the population had soared to two thousand.
Not long after, news about Melaka becoming a center of trade and commerce reached China. Yung-Lo, the Emperor of China who reigned from 1402 till 1424 send his envoy known as Ying Ching to Melaka in 1405. Yin Ching?s visit opened the way for the establishment of friendly relations between Melaka and China. Chinese merchants began calling at the port of Melaka and they can be said to be among the first traders to set up bases here. When the envoy of Melaka paid homage to the Emperor of China, the emperor praised Parameswara and acknowledged him as the rightful ruler of Melaka. Emperor Yung Lo then presented Parameswara with a seal, silk and a yellow umbrella as a symbol of royalty and also a letter appointing Parameswara as the ruler of Melaka. Melaka was then recognized as a kingdom by the Emperor of China. The envoy returned to Melaka together with a fleet led by Admiral Cheng Ho who was the first Chinese man to sail and explore the areas in the southern region.
It was during Parameswara?s reign that a large number of Javanese, Indians, Chinese, Burmese and other foreigners came to settle in Melaka. In 1409, Parameswara was converted into a Muslim and adopted the name Parameswara Iskandar Syah. Two years later, in 1411, Parameswara Iskandar Syah himself, his wife and son with a royal party of 540 people left for China with Admiral Cheng Ho to pay homage to Emperor Yung Lo.
In 1414, Parameswara passed away and was believed to be buried on top of a hill in Tanjung Tuan, which was also known as Cape Rachado. Parameswara had turned Melaka into a flourishing trading center during his twenty years reign in Melaka. He also established a strong relationship with the Emperor of China by sending six envoys to China.