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) Charles Stuart fled to the Hebrides, pursued by the British who put a reward of £30,000 (by the 21st century an approximate sum of £15 million) on his head. He eventually managed to escape to France and never stepped foot in Scotland again. (PROSE: A History of Humankind)
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)