Early career Webster made his first-team debut for
York City against
Burton Albion in the
Conference National on 29 December 2004. He made four appearances in
2006–07, After his release, Webster contemplated retiring and enrolling in university. He signed for
Conference North club
Harrogate Town in the same month and made his debut against
Scarborough in a 1–0 home defeat on 3 February 2007. He made his debut in a 5–2 defeat against
Baník Ostrava on 11 August 2007. The 2007–08 concluded with Most suffering
relegation to the
Czech 2. Liga, although Webster signed a new two-year contract with the club. He started a trial spell at
Scottish Premier League club
Motherwell in December 2008. The club entered negotiations over a deal for Webster to sign on
loan for the rest of the
2008–09 season.
Doncaster Rovers Webster had a trial with
Bury in July 2009, before leaving to trial with
Doncaster Rovers. He gave a "composed performance" in a pre-season
friendly against
Wolverhampton Wanderers and Doncaster
manager Sean O'Driscoll was looking to complete a deal for him to sign for the club. He eventually signed for the
Championship club on an initial two-year contract for an undisclosed fee on 5 August 2009. Webster made his Doncaster debut in a 1–0 victory away to
Notts County in the
League Cup first round on 11 August 2009.
Northampton Town On 17 March 2011, Webster joined League Two club
Northampton Town on loan until the end of
2010–11. On 17 May 2011, Webster was released by Doncaster and on the same day Northampton signed him permanently on a two-year contract.
Yeovil Town On 4 July 2012, Webster's contract with Northampton Town was terminated by mutual consent and later that day signed for
League One club
Yeovil Town on a two-year contract. He scored his first goal for Yeovil in 2–1 victory over Bury, after an attempted clearance from a corner struck him, sending it into the goal. Webster played in the 2–1 victory over
Brentford in the
2013 League One play-off final at
Wembley Stadium on 19 May 2013, seeing Yeovil win promotion to the
Championship for the first time in their history. He finished
2012–13 with 53 appearances and five goals for Yeovil.
Millwall Webster turned down a new contract with Yeovil to sign a two-year contract with Championship club
Millwall on 24 June 2014. On 19 February 2015, Webster returned to Yeovil Town on loan until the end of the 2014–15 season. On 20 May 2017, Webster started for Millwall as they beat
Bradford City 1–0 at Wembley Stadium in the
2017 League One play-off final, earning promotion back to the Championship after a two-year absence. He was offered a new contract by Millwall at the end of the
2017–18 season.
Scunthorpe United Webster signed for League One club
Scunthorpe United on 4 January 2019 on a contract until the end of the
2018–19 season. He was released by Scunthorpe at the end of
2018–19.
Carlisle United Webster signed for League Two club
Carlisle United on 24 June 2019 a one-year contract.
Bromley On 7 September 2020, it was announced that Webster had signed for National League Club
Bromley, linking up with former
Millwall teammate
Alan Dunne. On 5 May 2024, Webster captained Bromley to victory in the
2024 National League play-off final, scoring the winning penalty in the shootout as the club reached the Football League for the first time in their history. On 13 May 2025 the club said the player had signed a new deal. On 27 April 2026, following the club having secured promotion to League One, he announced that he would be departing the club upon the expiry of his contract at the end of the
2025–26 season. ==Career statistics==