His father took up medicine and qualified at St Mary's Hospital, Paddington where he met Oliver's mother who came from Lincolnshire.
He attended Denstone College like his father and had science on his curriculum, but also was a cross country runner and skilled marksman in the winter season.
Towards the end of this college period his father accompanied him to Jaguar Cars in Coventry to discuss an apprenticeship.
At Jaguar, Winterbottom was part of the team that designed the XJ21 prototype that never reached production.
[citation needed] Winterbottom later became an automotive consultant and served as membership director for the Coalition of Small Volume Automobile Manufacturers.