Whitehead was a right-handed lower-order batsman and a right-arm bowler who could bowl both off-breaks and medium-pace.

[7] Whitehead's success brought him selection for one of the representative sides in a non-Test cricket season: he played for A. J. Webbe's XI alongside notables such as Lord Hawke and F. S. Jackson against Cambridge University and took eight wickets in the game.

In 1904, Whitehead was awarded a joint benefit match by Warwickshire with Walter Richards, another player whose county career straddled the transition to first-class status; the match selected was the three-day game against Essex, starting on Monday 6 June.

[2] A newspaper report later that week, however, states that at the end of the match on the Wednesday evening, "he complained of feeling unwell, but his colleagues thought he was suffering from the effects of excitement".

[9] Further explanation came from an inquest held the following week: Whitehead, the inquest heard, had drunk some "stale beer" while playing for Stratford Cricket Club on the Saturday preceding his benefit match and that, combined with consumption (tuberculosis), had produced "acute gastro enteritis" which was cited as the cause of death.