1746

On 16 April 1746, the Jacobite Rising of 1745, led by Bonnie Prince Charlie, came to an end with the Jacobite defeat at the Battle of Culloden. In the aftermath of the battle, the Second Doctor, Jamie McCrimmon, Ben Jackson and Polly Wright closed down a slave trading operation run by Solicitor Grey. Jamie joined the Doctor on his travels. (TV: The Highlanders)

After travelling with the Doctor for several years, Jamie was returned by the Time Lords to Scotland at a moment shortly before he first boarded the TARDIS. His memories of his travels with the Second Doctor were erased. (TV: The War Games)

Jared Khan missed another chance to steal the Doctor's TARDIS, his first since 1289. He travelled to France, where he posed as the Count Cagliostro. (PROSE: Birthright)

Alternate timeline
In an alternate timeline accidentally created by Jamie in 1688, the Glorious Revolution was a failure and King James II remained on the throne until his death. Consequently, the Battle of Culloden never took place. In 1788, the version of Jamie native to this timeline told a Time Lord agent of the CIA that no battle had ever been fought at Culloden. (AUDIO: The Glorious Revolution)

Behind the scenes
One possible "game over" for the video game Don't Blink has the player being sent back in time by a Weeping Angel to the year 1746 to die in the Battle of Culloden.