The Battle of Culloden took place on Culloden Moor on 16 April 1746. It was the climactic battle of the Jacobite Rising. The British Army defeated the Scottish uprising led by Charles Edward Stuart, better known as Bonnie Prince Charlie.
Jamie McCrimmon took part in the battle alongside his laird Colin McLaren, and Colin's son Alexander McLaren. The Second Doctor, Polly Wright and Ben Jackson arrived in Scotland the day after the battle. Jamie witnessed the Prince fleeing from the site of the battle not long after it had ended. (TV: The Highlanders) He was dressed as a washerwoman as he fled. (AUDIO: Night's Black Agents)
Reverend Merodach contemptuously referred to the Prince as "an Italian dandy." (AUDIO: Night's Black Agents)
Alternative timeline
In an alternative timeline accidentally created by Jamie, the Glorious Revolution of 1688 was a failure and King James II retained the throne until his death. Consequently, the Jacobite Rising and the Battle of Culloden never took place. Bonnie Prince Charlie, who was James II's grandson, eventually ascended the throne as King Charles III. He was still the reigning monarch in 1788. In that year, 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.