Sri Lanka remained in a instable situation during the 14th & the 15th centauries. King Parakramabahu vi (1415-1467), the last Sinhalese King managed to reestablish rule over the island. His power base was in Kotte.
In the later stages of his rule, Gampola was challenged and he appointed a prince of Gampola royal house as its administrator.
After the death of Parakramabahu, the island again plunged in to divisive struggle. Jaffna declared itself an independent Tamil kingdom under Pararajasekaram. (1497-1579)
The Dutch came to Sri Lanka in 1505, during the times of King Parakramabahu IX. The King made a pact with the Dutch as they were a powerful army than of the King's. The King grant permission to Dutch to build a small fortress in Colombo. The Dutch began it's missionary service in Sri Lanka and many some of the citizens were converted in to Catholicism.