Woodward signed his first professional contract with Crewe in July 1992, and made his first team debut in April 1994, coming on as a substitute in a Third Division match at Walsall. He made his first professional start on 17 August 1993, playing in a League Cup tie against Wrexham at Gresty Road. He joined Bury in March 1997 and played for the Lancashire club 134 times in three years. He scored his first league goal on 26 December 1998 against his former club, Crewe, in a 3–1 defeat at Gresty Road. He was then signed by Sheffield United in March 2000. He played only four games for the Blades, and had two loan spells at Scunthorpe, before joining Halifax Town in the summer of 2001. When Halifax went into administration in the summer of 2002, Woodward was sacked, and subsequently joined Northwich Victoria.
Police career
Andrew Woodward joined the Lancashire police force after retiring from football, eventually leaving the force in November 2016. He was dismissed for gross misconduct following an inappropriate relationship with a family member of a victim.
Victim of sex abuse
Later in November 2016, it was reported that Woodward had been a victim of repeated child sexual abuse by Barry Bennell while a trainee at Crewe Alexandra in the 1980s. Woodward later claimed "People should know I suffered more than one abuser". In Manchester on 5 December 2016, Woodward was one of five abuse victims at the launch of an organisation, the Offside Trust, to support player victims of abuse and their families. Initially a director of the Trust, Woodward resigned on 27 January 2017. In October 2017, Woodward criticised Football Association chairman Greg Clarke for 'humiliating' remarks Clarke made to a Digital, Culture, Media and Sport Committee hearing, while the Professional Footballers' Association's chief executiveGordon Taylor said the PFA might sue Clarke over suggestions Taylor had not supported Woodward with further counselling. In December 2017, two men from Crewe were jailed for 'trolling' Woodward on social media. In June 2019, shortly before publication of Andy Woodward's biography, The Guardian reported that Barry Bennell's cousin, Ronald Bennell, had been jailed in 1971 for the murder of Woodward's aunt, Lynda Stewart, and that Barry Bennell had married Woodward's older sister, also named Lynda, in 1991. The Guardian's coverage also said Woodward unsuccessfully sued Crewe for damages in 2004. Woodward's book, Position of Trust, was shortlisted for the 2019 William Hill Sports Book of the Year.