Whitehead played at Sturt with his brother Reg and they were both followers in the 1926 premiership winning team.[3] He was club captain in the 1928 season.
In 1932 he returned to Melbourne to spend a season with St Kilda, but resigned in early August, citing his dissatisfaction at having been demoted to the reserves.[4]
Sturt (SANFL)
He finished his career back at Sturt, where he played for two more years.
South Australia 7.10 (52) def by. Victoria 9.12 (66), at Jubilee Oval, 29 April 1921 Western Australia 12.13 (75) def South Australia 9.11 (65), at Perth Oval, 13 August 1921 South Australia (43) def by. Victoria (78), at Fremantle Oval, 7 August 1921