King Senasammatha Wickramabahu expanded the Kandyan Kingdom to Siduruwana, Balavita, Sarasiya paththuwa, Matale, Atasiya paththuwa, Godarata, Mathurata, Uva, Atapodiya, Sorabora, Vellassa, Kothmale, Gampola, Dolosbage, Bulathgama, Mahathota, Trincomalee and Batticoloa. His stone script at Gadaladeniya states that, during 1472, he won the hearts of the chiefs of Sathkoralaya and added Kaluthara to his kingdom. Yet, kings of Kotte kingdom tried to defeat the kings of Kandy. The Seethawaka Kingdom too challenged Kandy. As a precaution, the Kandyan King seeked support from Portuguese and Portuguese who were aimed at earning profits from trade and spreading Cathilicism made use of this opportunity. King Jayaweera, who reigned Kandy from 1511 consented to pay taxes and to convert to Catholicism if they provided support.
Meanwhile, Menawara Thunaya, a nephew of Dodamwela Parakrama epa administrated Sathara koralaya, was against the king and ruled Udarata, making Pallepitiya as his administrative capital. By 1494, he expanded his territory to Gampola-Siduruwana, Balanvita, Mathalaya, Pansiyapaththuwa and Uva. Later on, king Parakramabahu VIII of Kotte captured this kingdom and the chiefs of Kanda Udarata Pasrata, including Menawara Thunaya consented to accept the Kotte kiongdom. Thus, the independent kingdom of Kandy for about 30 years, surrended again. Menawara Thunaya, was named as the king Thunayama and ruled Kandy as a tax paying king to the Kotte Kingdom.
After the king Thunayama, a prince of the family of the king Senasammatha Wickramabahu became thr king as Jayaweera II in 1514. He obtained support from the king of Kotte as well as from Potuguese and was married to a princess of the Kotte royal family.
In 1542, the chiefs of Kandy chased the king Jayaweera II from the throne and places the Prince Rankodi Pathirannehelage, the son of the king Thunayama on the throne, in the name, Weera Parakramabahu. He built the Poyamalu Viharaya and during his reign, a higher ordination ceremony was held at Getambe with the participation of 500 monks. And he appointed ven. Devalegala Rathanasara as the chief monk (Mahasami) in 1564. The Asgiri palmleaf states that the king died in 1579.
Thereafter, the son of the king Jayaweera II, Karalliyadde Bandara, came with a Portuguese army from Colombo and became the king in the name Jayaweera III in 1580. He was a catholic and he baptized his eldest daughter as Dona MAgarida and she was married to the King Dharmapala of Kotte.
After two unsuccessful efforts to capture Kandy in 1574 and 1578, King Rajasinghe I, the sin of King Mayadunne of Sitavaka captured kandy in 1582 and banished Karalliyadde Bandara . He was supported by the chiefs if Kandy lead by Virasundara mudali, who were against the king, because the king Karalliyadde Bandara was a catholic. He fled to Portuguese for protection, along with his daughter Kusumasana Devi and nephew Yamasinghe Bandara. Portuguese baptized them under the names Dona Catherina and Don Phillip. Karalliyadde Bandara dies in the meantime.
Meanwhile, King Rajasinghe I, killed Weerasundara mudali by a conspiracy. Thus his son, Konappu Bandara fled to Portuguese.
Due to the tyrannical activities pursued by the king Rajasinghe I in the Kandyan Kingdom. There was a strong discontentment towards him in the region. Meanwhile, were informed that king Rajasinghe was making plans to attack Colombo fort and in order to distract him, they dispatched an army to the hill country under Konappu Bandara alias Don Juan and placed Yamasinghe Bandara alias Don phillip on the throne.