Roy Whittaker attended Cheadle Hulme School, and first played lacrosse in 1928 at the age of 10. He also played cricket for the school first XI and was later a member of the Sale Cricket Club. After leaving school, he played lacrosse for the Old Waconians, and scored five goals on his début as a 17-year-old. At the outbreak of World War II, Whittaker joined the Manchester Regiment. During his time in the Army he played football, rugby and hockey for his regiment, before his demobilisation in 1946. Whittaker played for Lancashire and The Noth, and was a member of the highly successful Old Waconians team in the immediate post-war years. In the 1948 Olympic match against Rensselaer Polytechnic Institute Whittaker scored three goals in the 5-5 draw.