Phelip's uncle Sir Thomas Erpingham had been into exile with Henry Bolingbroke, and played a leading role in Bolingbroke's overthrow of King Richard II to take the throne as King Henry IV in 1399.
Through Erpingham's favour with the king, John Phelip entered the household of his heir, the future Henry V, becoming his close friend.
In 1411, he served as a captain in the army commanded by the Earl of Arundel, sent to France by Henry to support the Burgundians in the Armagnac–Burgundian Civil War.
Phelip raised a force of 30 men-at-arms and 90 archers before returning to France, and fought at the Siege of Harfleur, but succumbed to dysentery and died on 2 October 1415.
[1] He is buried at St Mary and All Saints' Church, Kidderminster, alongside his second wife Matilda Harcourt.