Pandyan Empire in the context of "Three Crowned Kings"

Indo-Roman trade relations (see also the spice trade and incense road) was trade between the Indian subcontinent and the Roman Empire in Europe and the Mediterranean Sea. Trade through the overland caravan routes via Asia Minor and the Middle East, though at a relative trickle compared to later times, preceded the southern trade route via the Red Sea, which started around the beginning of the Common Era (CE), following the reign of Augustus and his conquest of Egypt in 30 BCE.

The southern route so helped enhance trade between the ancient Roman Empire and the Indian subcontinent, that Roman politicians and historians are on record decrying the loss of silver and gold to buy silk to pamper Roman wives, and the southern route grew to eclipse and then totally supplant the overland trade route. Roman and Greek traders frequented the ancient Tamil country, present day Southern India and Sri Lanka, securing trade with the seafaring Tamil states of the Pandyan, Chola and Chera dynasties and establishing trading settlements which secured trade with the Indian subcontinent by the Greco-Roman world since the time of the Ptolemaic dynasty a few decades before the start of the Common Era and remained long after the fall of the Western Roman Empire.

The region of Tamil Nadu in the southeast of modern India, shows evidence of having had continuous human habitation from 15,000 BCE to 10,000 BCE. Throughout its history, spanning the early Upper Paleolithic age to modern times, this region has coexisted with various external cultures.

The three ancient Tamil dynasties namely Chera, Chola, and Pandya were of ancient origins. Together they ruled over this land with a unique culture and language, contributing to the growth of some of the oldest extant literature in the world. These three dynasties were in constant struggle with each other vying for hegemony over the land. Invasion by the Kalabhras during the 3rd century disturbed the traditional order of the land, displacing the three ruling kingdoms. These occupiers were overthrown by the resurgence of the Pandyas and the Pallavas, who restored the traditional kingdoms. The Cholas who re-emerged from obscurity in the 9th century by defeating the Pallavas and the Pandyas rose to become a great power and extended their empire over the entire southern peninsula. At its height the Chola empire spanned almost 3,600,000 km² (1,389,968 sq mi) straddling the Bay of Bengal. The Chola navy held sway over the Sri Vijaya kingdom in Southeast Asia.

The Jaffna Kingdom (Tamil: யாழ்ப்பாண அரசு, Sinhala: යාපනය රාජධානිය; 1215–1619 CE), also known as Kingdom of Aryachakravarti, was a historical kingdom of what today is northern Sri Lanka. It came into existence around the town of Jaffna on the Jaffna peninsula and was traditionally thought to have been established after the invasion of Kalinga Magha from Kalinga in India. Established as a powerful force in the north, northeast and west of the island, it eventually became a tribute-paying feudatory of the Pandyan Empire in modern South India in 1258, gaining independence when the last Pandyan ruler of Madurai was defeated and expelled in 1323 by Malik Kafur, the army general of the Delhi Sultanate. For a brief period in the early to mid-14th century it was an ascendant power in the island of Sri Lanka, to which all regional kingdoms accepted subordination. However, the kingdom was overpowered by the rival Kotte kingdom around 1450 when it was invaded by Prince Sapumal under the orders of Parakramabahu VI.

It gained independence from kingdom of Kotte control in 1467 after Kanakasooriya Cinkaiariyan and his two son's returned from Madurai with mercenaries to wrest the Jaffna Kingdom from Kotte's over lordship. and its subsequent rulers directed their energies towards consolidating its economic potential by maximising revenue from pearls, elephant exports and land revenue. It was less feudal than most of the other regional kingdoms on the island of Sri Lanka of the period. During this period, important local Tamil literature was produced and Hindu temples were built, including an academy for language advancement. The Sinhalese Nampota dated in its present form to the 14th or 15th century CE suggests that the whole of the Jaffna kingdom, including parts of the modern Trincomalee District, was recognised as a Tamil region by the name Demala-pattanama (Tamil city). In this work, a number of villages that are now situated in the Jaffna, Mullaitivu and Trincomalee districts are mentioned as places in Demala-pattanama.