Thackeray was part of the Manchester City youth team which won the FA Youth Cup in 1986, but moved on to Huddersfield Town without appearing for City's first team. He played only twice for Huddersfield, then spent a season with Newport County, before making more than 150 league appearances for each of his next two employers, Wrexham and Rochdale. In the 1997–98 season he helped Halifax Town to promotion from the Conference and played one more season in the Football League. Thackeray then returned to the Conference, spending four seasons with Nuneaton Borough. In 2003 he joined Ashton United, where he scored 5 goals from 91 games in all competitions, and for a time acted as assistant manager. His final club before retirement was Mossley, where he scored 4 goals from 74 games, and won the Player of the Year award in helping them to the Northern Premier League Division One title in the 2005–06 season.