He spent his early football career in the North East of England as a youth player, whilst training as a marine engineer, later working in that role for Hawthorn Leslie & Co of Tyneside.

[5] In the meantime, he had continued playing football for his regiment, and after serving his country in World War I, Whittaker forwent his engineering career and joined Leslie Knighton's Arsenal in November 1919.

He signed as a professional in January 1920 and made his debut in a 1–0 defeat away to West Bromwich Albion on 6 April 1920 and became a regular in the side in the 1920s, playing 70 times for the club and scoring two goals.

[5] After Chapman's death in 1934, Whittaker continued to serve under his successor, George Allison, and also became a trainer for the England national team.

The Second World War saw Whittaker work as an ARP warden, before becoming a pilot in the Royal Air Force, achieving the rank of squadron leader.