The Battle of Bosworth (1485): The Battle that ended the Middle Ages in England
- Chris Livemore
- 18h
- 3 min read

By Chris Livemore
By the summer of 1485, England had spent decades trapped in a bitter struggle between rival branches of the royal family. Kings had been deposed. Princes had strangely disappeared. Noble families had changed sides repeatedly. Nobody seemed entirely sure who would be in charge from one year to the next.
Then came Bosworth, which saw the death of a king and beginning of a new dynasty that would forever change England.
The Battle of Bosworth Field was fought on 22 August 1485 between King Richard III and Henry Tudor, a claimant whose connection to the throne was, if we're being honest, not particularly strong. He had been an exile in France for years, while Richard was the reigning king. He was an experienced military commander and had spent much of his life fighting. Richard should have won, but history doesn't always follow the bookies' favourite!
The armies met in Leicestershire. Richard had the larger force, but there was a problem.
Several powerful noble families were present with armies of their own and nobody was entirely certain whose side they were actually on. Not really ideal just before the start of an important battle, I mean who do you point your sword at for starters?
Most important were the Stanley family. Thomas Stanley and Sir William Stanley commanded thousands of troops and had deliberately positioned themselves where they could observe the battle without immediately committing to either side. Modern politicians call this keeping your options open. Medieval chroniclers called it something less polite.
The battle began with Richard's forces gaining the advantage. Henry's army was under pressure, and for a time it appeared that the king might secure victory. Then Richard saw an opportunity.
Henry Tudor had moved closer to the fighting than was perhaps wise. Surrounded by only a small bodyguard, he was suddenly vulnerable. Richard made a decision that has echoed through history ever since. Rather than continue directing the battle, he launched a cavalry charge straight at Henry.
And it almost worked. But as we will see, 'almost' doesn't quite cut it in battles.
Richard and his household knights cut through several opponents and came remarkably close to reaching Henry himself. One of Henry's standard bearers was killed. For a few moments the entire future of England hung on whether Richard could fight his way through the last defenders. Then everything changed.
The Stanleys finally committed their forces. Unfortunately for Richard, they chose Henry's side.
The king and his followers found themselves surrounded.
Richard fought on foot after his horse became trapped or was killed beneath him. According to later accounts, he refused opportunities to flee. Instead, he kept fighting. He was cut down within sight of the man he was trying to reach and with that, Richard III became the last English king to die in battle.
His crown, according to tradition, was found in a hawthorn bush and placed upon Henry Tudor's head. The Wars of the Roses were not quite over, but Bosworth effectively ended Plantagenet rule and made Henry Tudor king. The Tudor age had begun.
The consequences were enormous. Henry VII brought a measure of stability to a kingdom exhausted by civil war. His son would become Henry VIII. His granddaughter would become Elizabeth I.
The Tudors would oversee the English Reformation, the defeat of the Spanish Armada, and the foundations of England's rise as a major European power.
All of it traces back, in one way or another, to Bosworth.
The battle is often described as the end of the Middle Ages in England. Like all historical labels, that is a simplification. Medieval life did not suddenly stop on the evening of 22 August 1485.
But something undeniably changed.
The age of knights, feudal loyalties and Plantagenet kings gave way to a new world of stronger monarchies, growing bureaucracy and the first stirrings of modern England. Bosworth was not England's largest medieval battle. It wasn't even its bloodiest. But few battles in English history have had greater consequences.
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