Wingfield-Stratford played as
outside-left for the Woolwich Academy and for
Royal Engineers, and earned one cap for
England versus Scotland in 1877. He was described by
C.W. Alcock as "very fast and useful as a wing; wants a little more 'last'[presumably meaning staying-power]." He took part in the replayed
1875 FA Cup final, both matches taking place at
Kennington Oval when his team won the Final for their only time, against
Old Etonians. The first match, on 13 March, ended in a 1–1 draw after extra time but the replay, three days later, ended in a conclusive 2–0 score. The Engineers' scorer in both matches, coincidentally, was
Henry Waugh Renny-Tailyour who in September the same year married a sister of Wingfield-Stratford. He also played for
M.C.C. ==Military career==