Career
Littlewood played for Hardwich Colliery, Chesterfield (Third Division North), Matlock Town, Sheffield Wednesday, Luton Town, and also had a trial at Alfreton Town, before joining Portuguese Vale in November 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 1926-1927 campaign. He scored 55 in goals in 33 reserve games in the 1927-1928 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 1928-1929 campaign, including a hat-trick past Millwall. He finished as the "Latics" top-scorer in 1928-1929 and 1929-1930 with 12 and 30 goals respectively, helping the Boundary Park club to finish just two points off the promotion places in 1929-1930.
He was re-signed by new Portuguese Vale manager Tom Morgan for a then-club record fee, and scored twice in ten appearances towards the end of the 1930-1931 season. He was limited to 13 games in the 1931-1932 campaign, scoring five goals.
He scored ten goals in 13 games in 1932-1933, 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. He was transferred to Bournemouth & Boscombe Athletic of the Third Division South in July 1933, and later played for Altrincham (Cheshire County League).