This article re-examines speculations about school affiliation of the Milindapañha (Questions of King Milinda) and traces its presence from North West India in the early centuries CE up to Southeast Asia in the nineteenth century. As there are significant differences between the textual traditions of the Pali Text Society’s Milindapañho and the Siamese printed edition, the Milindapañh?, I will discuss the little-known textual characteristics of the Siamese recensions which were circulating in Central Siam from at least the seventeenth century. This is possible with the discovery of several Ayutthaya period Milindapañha manuscripts kept at a temple and the National Library of Thailand. By the end of the eighteenth century, at least three different recensions were circulating in Central Siam. This paper will present some of their dissimilarities as well as their probable textual lineages. The newly discovered manuscripts also partly demonstrate that the shape of the textual tradition of a text, at least for the Milindapañha in Siam, reflects a function of the textual community that preserved and transmitted it.