In 1347, Sri Teri Buana was succeeded by Sri Wikrama Wira.
 The increasingly powerful Javanese kingdom of Majapahit, the successor of Singhasari, began eyeing the growing influence of the tiny island kingdom.
Under the leadership of its ambitious warlord, Gajah Mada, Majapahit started to embark on overseas expansions against all kingdoms of Nusantara including the remnants of the Srivijaya.
In 1350, Hayam Wuruk ascended to the throne of Majapahit.
The new king sent an envoy to Singapura demanding the submission of the tiny kingdom.
Wikrama Wira refused to do so and even sent a symbolic message threatening to shave the Majapahit king's head should he proceed to Singapura.

The furious Majapahit king ordered an invasion with a fleet of 100 main warships (jong) and innumerable smaller vessels under the command of Damang Wiraja.
The fleet passed through the island of Bintan, from where the news spread to Singapura.
The defenders immediately assembled 400 warships to face the invasion.
Both sides clashed on the coast of Singapura in a battle that took place in three days.
Many were slain on both sides, however in the evening of the third day, the Javanese were driven back to their ships.
In 1347, Sri Teri Buana was succeeded by Sri Wikrama Wira.  The increasingly powerful Javanese kingdom of Majapahit, the successor of Singhasari, began eyeing the growing influence of the tiny island kingdom. Under the leadership of its ambitious warlord, Gajah Mada, Majapahit started to embark on overseas expansions against all kingdoms of Nusantara including the remnants of the Srivijaya. In 1350, Hayam Wuruk ascended to the throne of Majapahit. The new king sent an envoy to Singapura demanding the submission of the tiny kingdom. Wikrama Wira refused to do so and even sent a symbolic message threatening to shave the Majapahit king's head should he proceed to Singapura.
The furious Majapahit king ordered an invasion with a fleet of 100 main warships (jong) and innumerable smaller vessels under the command of Damang Wiraja. The fleet passed through the island of Bintan, from where the news spread to Singapura. The defenders immediately assembled 400 warships to face the invasion. Both sides clashed on the coast of Singapura in a battle that took place in three days. Many were slain on both sides, however in the evening of the third day, the Javanese were driven back to their ships.
Kingdom of Singapura