A powerfully built and prolific goalscoring inside-forward, Whittingham started with amateur side
Goldenhill Wanderers before signing for
Stoke (without making a first-team appearance) and later
Crewe Alexandra. He later moved on to
Blackpool, where he stayed for just a year. He scored 28 goals in 53 league games, becoming the
club's top goalscorer over two terms (he achieved the feat in
the latter season despite his leaving
Bloomfield Road midway through the campaign). In January 1909, he joined
First Division side
Bradford City and scored 11 goals in nine games to save the "Bantams" from
relegation at the expense of
Manchester City. He then equalled a then-club-record 21 league goals during the
1909–10 season. His performances at
Valley Parade earned him a move to
David Calderhead's relegation-threatened
Chelsea in April 1910 – for a fee of £1,300. He made an appearance for the
Football League XI in February 1919 against the
Scottish League at
St Andrew's,
Birmingham, in the first representative match played after the First World War, and scored the second goal in a 3–1 win; according to the
Daily Express reporter, "the pick" of the English XI were Whittingham,
Billy Morgan, and
Joe Clennell. He returned to Chelsea after the war, playing six more games in the
1919–20 season, finishing his time with the club with a record of 80 goals from 129 league and
FA Cup games. He then moved to Stoke again for a £500 fee, where he scored eight goals in 18 Second Division games in another brief spell at the
Victoria Ground. He later played for
Wrexham before returning to Goldenhill Wanderers. Despite his prolific goalscoring record, Whittingham was never
capped for
England, though he did feature in a Victory international against
Wales at the Victoria Ground on 18 October 1919. ==Style of play==