Hamilton, Lanarkshire born left half David Thackeray played junior football for Banknock in 1919 and Law Winnings in 1920 before joining Scottish League Alloa Athletic in 1921. His progress at Alloa saw him attract the attention of Motherwell, who signed him in the summer of 1925. Thackery made his ‘Well debut on 15th August 1925 against Clydebank at Fir Park, The Steelmen winning 2-1, and while with Motherwell he was a member of their team that finished runners up in The Scottish League in 1926-27. He represented The Scottish League in a 2-1 victory over The Irish League at Windsor Park, Belfast in October 1927 before joining First Division Portsmouth for £3,500 in the 1928 close season after 2 goals in 116 appearances for Motherwell.
He made his Football League debut for Pompey against Huddersfield Town the same August and missed two games all season as Pompey reached the 1929 FA Cup Final, where they were beaten 2-0 by Bolton Wanderers at Wembley. He continued to be a virtual ever present for another six seasons, becoming club captain, and returned to Wembley in the 1934 FA Cup Final, this time Portsmouth were beaten 2-1 by a late Fred Tilson brace for Manchester City. He lost his place in the Pompey line up in September 1935, probably through injury, and retired from the game having scored 10 goals in 308 appearances while at Fratton Park.