He married secondly in 1438, Katherine de la Pole (1416-1488, buried in Rowley Abbey, Oxfordshire), daughter and heiress to Sir Thomas de la Pole (aft. 1397-1433), who died in France while a hostage for his brother William, son to Michael de la Pole, 2nd Earl of Suffolk. They had two known daughters, the eldest, Elizabeth Stapleton, married before March 1464, Sir William Calthorpe, Knt., of Burnham Thorpe, Norfolk. The younger daughter, Jane (or Joan) Stapleton (d. 1519), married Sir Christopher Harcourt, Knt., of Great Ashby, (Ashby Magna), Leicestershire (d. 1474) and remarried John Hudleston (Huddleston), of Millom Castle appointed sheriff of Cumberland by the Duke of Gloucester and keeper and bailiff of the king's woods and chases in Barnoldswick, Yorkshire, steward of Penrith and warden of the west marches.
This marriage of Joan Stapleton who died in 1519 is linked to the wrong generation as is the Ann Stanley who is very nearly the same age as her supposed mother Margaret Neville(Huddleston/Thelkeld)