Abstract: Kalinga, a ruling entity in the Odisha region of South India since the Anuradhapura era, maintained cultural and political ties with Sri Lanka. This research examines the nature of the kingship relations between Kalinga and Sri Lanka, focusing on their objectives, outcomes, and political impact on both nations. The study employs a historical comparative methodology, utilizing inscriptions and primary and secondary literary sources. The earliest recorded connection between Sri Lanka and Kalinga is linked to the arrival of Prince Vijaya. According to the Mahavamsa, Vijaya maternal grandfather, King Vanga, married the daughter of the King of Kalinga. This suggests that Sri Lanka earliest ruling lineage had kinship ties with Kalinga. During the Anuradhapura period, King Mihindu IV initiated marital relations with Kalinga by marrying a Kalinga princess. His sons, Sena V and Mahinda V, later ascended the Sri Lankan throne. In the Polonnaruwa period, King Vijayabahu I appointed the Kalinga princess Tilokasundari as his chief consort. Their son, Prince Vikramabahu, married Princess Sundaradevi of Kalinga. Additionally, a son of Vijayabahu I sister, Princess Mitta, also married a Kalinga princess. According to inscriptions, King Nissankamalla, who ruled Polonnaruwa, was the son of Kalinga Parvati Devi and King Jayagopa. He married Subhadra Mahadevi of the Kalinga royal lineage, and their children were Veerabahu and Sarvagna Sundari. Nissankamalla inscriptions explicitly state that the Kalinga lineage descended from the Okkaka dynasty. Many Sri Lankan kings also mentioned in their inscriptions that they belonged to the Okkaka lineage. These marital alliances indicate the existence of strong kinship ties between Sri Lanka and Kalinga. Politically, these connections led to the placement of kin in high-ranking positions in both states, strengthening their administrative structures. Internationally, these alliances contributed to political stability. In times of politic