This English nobleman was the eldest son and heir of Sir Pain Tiptoft (died c. 1413) by his spouse, Agnes, née Wrothe (d. bef. 1413).
In 1413, he was heir to his first cousin, Elizabeth Wrothe, wife of Sir William Palton, Kt., by which he inherited the manors of Nether Wallop, Hampshire, Worcesters (in Enfield), Middlesex, and Redlynch (in Downton, Wiltshire).
His father, Sir Payn, was closely attached to Richard, earl of Arundel, one of the Lords Appellant of 1388, but he himself joined the household of another of their number, Henry of Bolingbroke, so that as a young esquire, between April and September 1397, he spent 125 days serving infra curia at a wage of 7½d.a day.
He continued in Henry's service right up to his exile, and it is highly probable that he and his father rallied to the Lancastrian banner soon after Bolingbroke's landing in Yorkshire to claim his birthright.
He was returned to Parliament as knight of the shire for Huntingdonshire in January and October, 1404 and again in 1406, when he was elected Speaker of the House of Commons.