The Caledonian Confederacy is a name given by historians to a group of disparate tribes inhabiting the Scottish Highlands at the time of the Roman occupation of Britain.

They were Pictish hillfort builders who combined forces on at least two occasions in an attempt to defeat the Roman army. In AD 83 or 84, led by Calgacus, they were defeated by Gnaeus Julius Agricola at Mons Graupius and in 209 they surrendered to Septimus Severus.

By 210 however, the Caledonians had revolted and formed an alliance with the Maeatae. A punitive expedition led by Severus' son, Caracalla was sent out with the purpose of slaughtering every Caledonian it encountered. Severus meanwhile prepared for conquest but already ill, he died at York in 211. Caracalla attempted to take over command but when his troops refused to recognise him as emperor, he made peace with the Caledonians and retreated south to press his claim for the throne.

The Caledonian Confederacy did not include the broch building peoples of the far north of Scotland who appear to have been in conflict with the Caledonians and probably more sympathetic to Rome.