Taylor-Fletcher began his senior career at Northwich Victoria in 1999, and made 43 league appearances whilst at the club. Towards the end of his time there, he had a brief loan spell with Hull City, before switching permanently to Leyton Orient in June 2001. He struggled to break into the Leyton Orient team, and spent a loan spell at Grays Athletic, and two at Dagenham & Redbridge. In August 2003, after 21 league appearances for Leyton Orient, Taylor-Fletcher joined Lincoln City; a successful spell saw him play 90 league games in two seasons. He then moved to Huddersfield Town in June 2005, making 81 league appearances in two seasons. Taylor-Fletcher then joined Blackpool in July 2007, and established himself as a regular player for the club. After 215 league appearances for Blackpool, he joined Leicester City in September 2013.