Wheatley Hill, County Durham born left half Ollie Thompson began his football career with Spen Black & White after the end of the First World War and played for Spennymoor United in 1920, from where he was signed by Third Division (South) club Merthyr Town, spending 1921-22 on their books without making a first team appearance. Thompson joined Third Division (North) club Chesterfield in the 1922 close season, making his Football League debut at Crewe Alexandra that September, immediately establishing himself as a regular for The Spireites. He helped them to finish fourth in the division in his debut season, and third in their 1923-24 campaign, when he missed only two matches.
Thompson was an ever present in their 1926-27 campaign, but after six seasons at Saltergate he left Chesterfield to join Queen’s Park Rangers in the 1928 close season after 4 goals in 235 appearances for The Spireites. He made 18 appearances for Rangers during a single season at Loftus Road but returned north to join newly elected Third Division (North) club York City in the summer of 1929, where he played in their inaugural League fixture at Wigan Borough that August and was an ever present in their maiden League campaign.
He missed only 5 matches over their following two seasons before a move to Halifax Town in the 1932 close season having scored twice in 133 matches for The Minstermen. Thompson missed just one match for The Shaymen in their 1932-33 campaign, he re-joined Chesterfield, and although he never made a further appearance for them he became their trainer and held that position until his retirement in 1966.