She was given a scholarship and a two-year professional contract by
Arsenal Ladies football team. Bailey came off the bench during Arsenal's win in the 2013 FA Cup. Bailey started the 2014 FA Cup final and was part of the Arsenal side which won 2–0. In April 2015, Manchester City's England midfielder
Jill Scott was shown the
red card and banned for three matches for headbutting Bailey during a match. Bailey transferred to Chelsea in 2016 and made 16 appearances in her first season, as a deep-lying midfielder and sometimes in central defence. She suffered an
anterior cruciate ligament injury in April 2017, ruling her out of participation in the following season. In January 2019, Chelsea gave Bailey a one-year contract extension and sent her on loan to
Reading to prove her fitness. In July 2019 Bailey was
transferred to
Liverpool, who assigned her the
number 8
shirt. She was released at the end of the 2021-22 season. On 4 February 2024, Bailey was announced at London City Lionesses. On 21 September 2024, Bailey was announced at Sheffield United. On 16 January 2026, Bailey joined
Damallsvenskan side
Piteå for the 2026 season. ==International career==