Yorkshireman Whitehead, coming from a wealthy background, gained from the wool industry, started racing in a Riley when he was 19.

He moved up to an ERA B-Type the following season and then scored the first major result for the Alta, when he finished third in the Limerick Grand Prix, a Formula Libre race.

[1][2][3][4][5][6] During World War II, Whitehead was a pilot with the Royal Air Force, and he was back in competition as soon as racing was revived, taking his trusty ERA to second place in the British Empire Trophy, held at the Douglas Circuit on the Isle of Man in the summer of 1947.

In doing so, he became the first Englishman to win a major international motor race outside of the United Kingdom since Richard Seaman.

[2][3][5][10] In 1953, Whitehead decided to concentrate on sports cars, and in July, he saw more success sharing a Jaguar C-Type with Stirling Moss in the 12 Heures Internationales de Reims.

He returned again in 1954, in a full works supported Jaguar D-Type to win the event again partnered by Ken Wharton.

[13][14] Whitehead's last great performance was at Le Mans in 1958 where he came second in an Aston Martin DB3S, sharing the driving with his half-brother, Graham.