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Although legendary accounts shroud Singapore's earliest history, chroniclers as far back as the second century alluded to towns or cities that may have been situated at that favored location. Some of the earliest records of this region are the reports of Chinese officials who served as envoys to the seaports and empires of the Nanyang (southern ocean--see Glossary), the Chinese term for Southeast Asia. The earliest first-hand account of Singapore appears in a geographical handbook written by the Chinese traveler Wang Dayuan in 1349. Wang noted that Singapore Island, which he called Tan-ma-hsi (Danmaxi), was a haven for several hundred boatloads of pirates who preyed on passing ships. He also described a settlement of Malay and Chinese living on a terraced hill known in Malay legend as Bukit Larangan (Forbidden Hill), the reported burial place of ancient kings. The fourteenth-century Javanese chronicle, the Nagarakertagama, also noted a settlement on Singapore Island, calling it Temasek.

A Malay seventeenth-century chronicle, the Sejarah Melayu (Malay Annals), recounts the founding of a great trading city on the island in 1299 by a ruler from Palembang, Sri Tri Buana, who named the city Singapura ("lion city") after sighting a strange beast that he took to be a lion. The prosperous Singapura, according to the Annals, in the mid-fourteenth century suffered raids by the expanding Javanese Majapahit Empire to the south and the emerging Thai kingdom of Ayutthaya to the north, both at various times claiming the island as a vassal state.

The Annals, as well as contemporaneous Portuguese accounts, note the arrival around 1388 of King Paramesvara from Palembang, who was fleeing Majapahit control. Although granted asylum by the ruler of Singapura, the king murdered his host and seized power. Within a few years, however, Majapahit or Thai forces again drove out Paramesvara, who fled northward to found eventually the great seaport and kingdom of Malacca. In 1414 Paramesvara converted to Islam and established the Malacca Sultanate, which in time controlled most of the Malay Peninsula, eastern Sumatra, and the islands between, including Singapura. Fighting ships for the sultanate were supplied by a senior Malaccan official based at Singapura. The city of Malacca served not only as the major seaport of the region in the fifteenth century, but also as the focal point for the dissemination of Islam throughout insular Southeast Asia.