On 2nd february1461, during the Wars of the Roses, a Lancastrian force, including Bretons and Frenchmen, was intercepted and defeated by the Yorkist Edward, Earl of March at the Battle of Mortimer's Cross, 25 kilometres north-west of Hereford. One of the Lancastrian leaders, Owen Tudor, was captured and taken into Hereford. Owen was a high-ranking nobleman - he had married Catherine of France, the widow of Henry V.

Legend tells that it was at the forerunner of the Green Dragon Hotel in Broad Street that Edward stayed with his prisoner after the battle. The next day Owen was taken out to be beheaded in the market place (High Town). At first Owen was unable to believe that he would be executed - but when the collar of his red velvet doublet was ripped off he accepted his fate saying "that head shall lie on the block that was wont to lie on Queen Catherine's lap". Owen was called ‘the handsomest man in England’, which might have inspired what followed. His head was placed on the market cross where a madwoman combed his hair and washed the blood from his face. She lit more than a hundred candles, which she placed around the cross. Owen's body was afterwards buried in a chapel of the Greyfriars priory just outside the town.

Owen Tudor was the great-grandfather of Henry VIII. Edward (later King Edward IV) was himself Henry's grandfather. Edward was back in Hereford that September, by now the battle of Towton had been fought and he was King of England.

Edward IV died in April 1483. A few months later his brother, Richard of Gloucester (Richard III) seized the throne and placed Edward's young sons, Edward V and Richard, in confinement - the 'Princes in the Tower'.

The Duke of Buckingham, at first Richard's strong supporter, rebelled and joined a local nobleman, Walter Devereux, at his castle at Weobley in Herefordshire. Marching south, Buckingham was deserted by his army, captured and executed. His son, Edward, was smuggled into Hereford by Elizabeth Delabeare and hidden there until safer times.

In 1485, Henry Tudor passed through Leominster on his way to victory at Bosworth and claiming the kingdom as Henry VII. The change of regime passed with little disturbance locally although eighteen people were bailed for one hundred pounds to appear before the new king's council, presumably to ensure that they would not cause trouble. In 1486 Henry visited Hereford during a tour of his new kingdom.

In 1493 a council was set up for Henry's eldest son, Arthur, prince of Wales. When Arthur died in 1502 the council continued to exist and evolved into the council of the Marches. This came to exercise de facto jurisdiction over north and south Wales and the counties of Shropshire, Herefordshire, Gloucestershire, Worcestershire Cheshire and Flint.

In 1536 the administration of Wales was re-organised. It was at this time that the border between Herefordshire and Wales took more or less its present form, assimilating the Welsh territory of Ewyas Lacy and other independent Marcher lordships - Clifford, Eardisley, Wigmore and others. Old and New Radnor, on the other hand, were taken out of Herefordshire and merged into the new county of Radnor.