He was the second son of Sir Everard Digby, Lord of Tilton and Drystoke in the County of Rutland.
[1] Sir Everard and four of his sons were killed at the 1461 Battle of Towton,[1] a part of the Wars of the Roses.
In 1477, Simon Digby was knighted by the Yorkist King Edward IV, but he fought eight years later on the victorious Lancastrian side at the Battle of Bosworth Field.
"[1] Simon de Montford was executed in 1495 for contributing to the fund of Perkin Warbeck, who was plotting to oust King Henry VII from the throne.
Simon Digby married Alice, heir of John Walleys of East Haddon, Devon.