Whipps Cross is first mentioned in local records of the late fourteenth century as Phip’s cross, referring to a wayside cross set up by a member of the family of a John Phyppe. Further versions on maps and deeds are Phyppys Crosse in 1517, Fypps Chrosse in 1537, Phippes Cross in 1572, and finally Whipps Cross by 1636. The change in the initial consonant is thought to have been a product of the local Essex dialect at that time, in which ’F’ sounds were pronounced as ’W’.

To the south of Whipps Cross Road and west of James Lane, the Forest House estate had its origins in a lease of land granted by the Abbot of Stratford Langthorne Abbey in 1492.

Forrest House was built by 1568. Ownership of the estate passed to James Houblon, a wealthy City merchant of Huguenot descent, in 1682. Houblon built a new house in the English Baroque style. In 1703, the estate was sold to Sir Gilbert Heathcote, the last Lord Mayor of London to ride on horseback at the Lord Mayor’s Show. The estate was later sold to the Bosanquet family in 1743, and it remained in their hands until 1889, when it was sold to the West Ham Board of Guardians who established a workhouse.

During World War I, the workhouse infirmary was used to treat wounded soldiers and this became Whipps Cross Hospital in 1917. Of notable births at the hospital’s maternity unit was one David Beckham.

The area to the south and west of Whipps Cross is residential, mainly terraced housing built in the late 19th and early 20th centuries. The boundary between Whipps Cross and Upper Walthamstow to the west and with Leytonstone to the south is ill-defined.

To the east of Whipps Cross is an area of Epping Forest called Leyton Flats, which features a lake created from old gravel pits called the Hollow Pond.

In 1905, a swimming pond was excavated by manual labour as part of an unemployment relief scheme, located to the north of the Hollow Pond. It was locally known as the ’Batho’. In 1932, a new open-air swimming pool, now called Whipps Cross Lido, was opened there by the Lord Mayor of London. By the 1980s, attendances had fallen and the decision was taken to close the lido on 4 September 1982. The site was levelled and returned to forest land.