Treeton, Rotherham, Yorkshire born centre forward Stewart Littlewood began his football career playing for Holmfield Mission and Hardwick Colliery in 1923, before he joined of the Chesterfield in January 1924. Having failed to make a first team appearance for The Spireites, he returned to non league football with Matlock Town in 1924. He joined Sheffield Wednesday in January 1925 and again spent the rest of the season on their books without making the first eleven.
He signed for Third Division (South) club Luton Town in July 1925 and made his Football League debut against Brighton & Hove Albion that October, scoring in a 3-3 draw. He scored two further goals in six more matches before losing his place in November, and he was released at the end of the 1925-26 season. After a trial at Alfreton Town in October 1926, he joined Second Division Port Vale in November, and while his scoring ratio was prolific, with Wilf Kirkham tearing up the goalscoring charts in the first team, his opportunities were limited. 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.
The next season he scored 55 in goals in 33 reserve games, however he was limited to just seven first team games despite scoring a hat-trick past Fulham in a 4-1 win at The Old Recreation Ground in February 1928. He all but continued his goal-a-game scoring ration in 1928-29, hitting nine goals in ten appearances at the start of the campaign, including a hat-trick against Millwall in September 1928, but still lost his place at the end of October before being bought by Oldham Athletic in exchange for Albert Pynegar and £1,300 in January 1929 after 18 goals in 19 appearances for Vale.
At Boundary Park he scored both goals on his debut in a 2-1 win over Preston North End and finished as The Latics’ topscorer in 1928-29 and 1929-30 with 12 and 28 goals respectively, which included a hat-trick in a 5-0 win over Stoke City in March 1930, helping Oldham to finish in third place, just two points off the promotion places in 1929-30.
After 47 goals in 81 appearances for Oldham Athletic, he was re-signed by new Port Vale manager Tom Morgan for a then club record fee of £1,550 in March 1931, and scored twice in ten appearances towards the end of the 1930-31 season. Injury limited him to 12 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. But among those he created a club record scoring six goals in one match, on 24th September 1932, in a 9-1 thrashing of Chesterfield at The Old Recreation Ground.
He was transferred to Third Division (South) club Bournemouth & Boscombe Athletic in July 1933 after 17 goals in 35 appearances in his second spell for Port Vale, but injury once again restricted him to 13 goals in 20 games for The Cherries, and despite a hat-trick in a 5-0 win over Bristol City at the end of March 1934 he was released from Dean Court at the end of the season.
He then signed with Cheshire County League side Altrincham in July. His injuries left him with restricted mobility, but he still managed to score 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 in 1937 he had a brief spell at Mossley and then a final injury-plagued season with Northwich Victoria before his retirement in 1938.