The fall of Singapura began with a personal vendetta. Iskandar Shah, the king, accused one of his concubines of adultery and humiliatingly stripped her in public. Seeking revenge, her father, Sang Rajuna Tapa, an official in Iskandar Shah's court, secretly informed the Majapahit king of his allegiance should there be an invasion on Singapura. In response, in 1398, Majapahit sent a vast fleet, leading to a siege on Singapura. While the fortress initially withstood the onslaught, deceit from within weakened its defenses. Sang Rajuna Tapa falsely claimed that food stores were empty, leading to starvation among the defenders. When the fortress gates eventually opened, Majapahit forces stormed in, resulting in a devastating massacre so intense that it's said the island's red soil stains are from the bloodshed.^[8]

Portuguese records present a contrasting narrative on the last ruler of Singapura. While the Malay Annals recognize the last ruler as Iskandar Shah, who later founded Malacca, Portuguese sources name him Parameswara, also referenced in Ming annals. The prevalent belief is that Iskandar Shah and Parameswara are the same individual.^[9] However, discrepancies arise as some Portuguese and Ming documents suggest that Iskandar Shah was actually Parameswara's son, who later became Malacca's second ruler.

Parameswara's backstory, as per Portuguese accounts, portrays him as a Palembang prince who contested the Javanese control over Palembang post-1360. After being ousted by the Javanese, Parameswara took refuge in Singapore and was greeted by its ruler, Sang Aji Sangesinga. However, Parameswara's ambition led him to assassinate Sang Aji just eight days later, subsequently ruling Singapura with the assistance of the Çelates or Orang Laut for five years.^[10] Yet, his reign was short-lived as he was expelled, possibly due to his previous assassination of Sang Aji, whose wife might have had affiliations with the Kingdom of Patani.^[11]