In 1535, the Portuguese captain of Malacca Dom Estevão da Gama attempted to defeat the Sultan of Johor by attacking his capital at Ugentana.

[1] Hence, he was able to rebuild his city and continue harassing the navigation of Malacca after the Portuguese had left, and for that reason Dom Estevão was compelled to try and attack Ugentana once more.

Having sailed up the Johor River, the Portuguese learned that the sultan had constructed a new stockade where a stone fort they destroyed the previous year had once stood, garrisoned by 5,000 men, a short distance from his capital.

[1] The sultan witnessed the battle from atop an elephant, and again attempted to evacuate into the jungle, but he suffered a revolt and his baggage train carrying his treasure was assaulted mid-retreat by his own fleeing forces.

[1] Under these conditions, he sought terms with the Portuguese, but Dom Estevão only agreed to sign a peace treaty after the sultan provided his uncle as a hostage.