Pain Tiptoft (also known as Pagan or Payn, Tiptoft or Tibetot), was born about 1279 to Robert Tiptoft and Eva de Chaworth. Robert was a captain of Edward I during the Welsh wars.
Pain first saw military service in 1300. He was made a Banneret in 1304 even though he had never been knighted – such a double promotion was highly unusual. Banneret was a level of status higher than that of a Knight and indicated a military leadership role, and this status was communicated by bearing arms on a square banner rather than the triangular pennon of the Knight Bachelor.
Pain Tiptoft fought and died at Bannockburn, killed in the leading English division along with the Earl of Gloucester and many other nobles. He had been married to Agnes, daughter of Lord William de Ros. They had a son, John (2nd Baron 1313-1367) who was only a year old at his father’s death.