The discovery follows a study of more than 5,000 flint artefacts recovered from fields at Howburn, near Biggar, from 2005 to 2009.
Experts observed striking similarities to previous finds in northern Germany and the south of Denmark, helping them date the tools to the very earliest part of the late-glacial period.
They now believe Howburn is likely to have hosted the very first settlers in Scotland.
Previously, the oldest evidence of human occupation could be dated to around 13,000 years ago at a now-destroyed cave site in Argyll.
It is thought the hunters who left behind the flint remains came into Scotland in pursuit of game, possibly wild horses and reindeer, at a time when the climate improved following severe glacial conditions.
These glacial conditions returned around 13,000 years ago and Scotland was once again depopulated, probably for another 1,000 years, after which new groups of people with different types of flint tools made an appearance.
Historians say the similarity in the design of the Howburn tools to those uncovered elsewhere in Europe offers "tantalising glimpses" of links between people across what would have been dry land, now drowned by the North Sea.
Alan Saville, a senior curator at the National Museums of Scotland and a specialist in the study of flaked flint and stone tools, said: "These tools represent a real connection with archaeological finds in north-west Germany, southern Denmark and north-west Holland, a connection not seen elsewhere in Britain at this time.
"This discovery is both intriguing and revolutionises our ideas about where humans came from in this very early period. In southern Britain, early links are with northern France and Belgium. Howburn is just one chance discovery and further such discoveries will no doubt emerge."
The findings were revealed today by the Scottish Culture Secretary in a speech at the Institute for Archaeologists' annual conference in Glasgow.
Fiona Hyslop announced around £1.4 million of funding for more than 60 projects this year and next through Historic Scotland's annual Archaeology Programme.
Ms Hyslop said: "Our heritage helps us to connect our past, present and future. It reveals stories about where we've come from and who we are, and helps us to reflect on who we could be.
"The discovery of the earliest physical evidence of human occupation in Scotland is hugely exciting, in part because it offers us a very tangible link to the past and a physical reminder of the people who came before us."