Early career Littlewood played for Holmfield Mission and Hardwich Colliery before he joined the
Chesterfield Third Division North in January 1924. Having failed to make a first-team appearance for the "Spireites", he returned to
non-League football with
Matlock Town. He gained another chance in the
English Football League with
Second Division side
Sheffield Wednesday in January 1925. Still, he left
Hillsborough at the end of the
1924–25 season without featuring in a first-team game. He signed with
Luton Town in July 1925 and scored two goals in six
Third Division South games before his release at the end of the
1925–26 season. He had a trial at
Alfreton Town in October 1926. He scored a brace on his debut at
Clapton Orient on Christmas Day 1926, but only made one further
Second Division appearance in the
1926–27 campaign. He scored 55 in goals in 33
reserve team games in the
1927–28 season. However, he had to battle out-of-form club legend
Wilf Kirkham for a first-team place, and was limited to just seven first-team games despite scoring a
hat-trick past
Fulham. He hit nine goals in ten appearances at the start of the
1928–29 campaign, including a hat-trick past
Millwall.
Oldham Athletic Littlewood was
transferred to Second Division side
Oldham Athletic, in exchange for
Albert Pynegar and £1,300, in January 1929. He finished as the "Latics"
top-scorer in
1928–29 and
1929–30 with 12 and 30 goals respectively, helping the
Boundary Park club to finish just two points off the
promotion places in 1929–30.
Return to Port Vale He was re-signed by new Port Vale
manager Tom Morgan for a then-
club record fee of £1,550, and scored twice in ten appearances towards the end of the
1930–31 season. He was limited to 13 games in the
1931–32 campaign, scoring five goals. He scored ten goals in 13 games in
1932–33, with his contribution limited after he was forced to undergo surgery to repair
cartilage damage on a twisted
knee. A club record six of his goals came in one match on 24 September, in a 9–1 thrashing of
Chesterfield at the
Old Recreation Ground.
Later career He was transferred to
Bournemouth & Boscombe Athletic of the
Third Division South in July 1933. Injury restricted him to 18 league games, during which he scored 11 goals, and he was released from
Dean Court at the end of the
1933–34 season. He signed with
Cheshire County League side
Altrincham in July 1934. His injuries restricted his mobility, but he scored 100 goals in 111 league and cup appearances. During his three seasons at
Moss Lane he scored seven goals in a 9–0 FA Cup win over
Moulton Verdon, hit four goals in games against
Buxton,
Tranmere Rovers Reserves,
Nantwich Town and
Hyde United, and scored hat-tricks past
Ashton National,
Prescot Cables,
Willaston and
Winsford United. After leaving the "Robins", he had one final injury-plagued season with
Northwich Victoria. ==Style of play==