Cutler was born in Perton, started his career as a seventeen-year-old at West Bromwich Albion having progressed through the FA National School of Excellence at Lilleshall. He went out on loan to gain experience at Coventry City, Tamworth and Chester City where he made his professional debut on 20 April 1996 in a 1–1 draw away at Torquay United. Cutler was sold to Crewe Alexandra in the summer of 1996 without playing a game for West Brom. He spent his entire spell at Crewe as understudy to Jason Kearton heading out on loan to Chester City, Cheltenham Town, Leek Town and Stalybridge Celtic. He then played for Chester City in 1998–99, after two previous loan spells with the club. During his time at Chester Cutler made 26 appearances under Kevin Ratcliffe and earned himself a move to Premier League side Aston Villa in October 1999. Cutler only made one appearance for Villa which came as a late substitute for the injured David James on 14 February 2000 against Middlesbrough with Villa winning 4–0. He spent time during the 2000–01 season on loan at Oxford United, making 11 appearances before being recalled in February 2001. He joined Stoke City in July 2001 and was initially going to be back-up to Gavin Ward but took his place in the team from September 2001. Cutler played 43 times in 2001–02 helping the team reach the 2002Football League Second Division play-off Final where they beat Brentford 2–0 to gain promotion to the First Division. He remained as first-choice going into the 2002–03 season but lost his place once Tony Pulis became manager in November 2002. In March 2003 he joined Swansea City on loan as cover for injured goalkeeper Roger Freestone. He played in the next 13 league games culminating in a superb performance against Hull City on the final day of the season which kept the Swans in the Football League. Cutler was back at Stoke for the 2003–04 season where he was back-up to Ed de Goey and made 16 appearances as the Potters finished in 11th position. Cutler joined League One side Stockport County in the summer of 2004 after turning down the chance to re-join Swansea. He made 27 appearances in 2004–05 as Stockport had a terrible campaign, finishing bottom of League One. He joined Rotherham United in August 2005. He spent two seasons with the Millers making 70 appearances before deciding to retire due to a persistent back injury.
Coaching career
He joined Bury as a goalkeeping coach and is part of Just4keepers goalkeeping coaching company. He re-registered as a player at the club in November 2010 and was given the number 30squad number, expecting to remain on the books on non-contract terms until the end of the 2010–11 season. On 31 March 2011, however, Cutler joined manager Alan Knill and Assistant ManagerChris Brass in leaving the club for Scunthorpe United. On 22 October 2011 Cutler was named on the substitute's bench in Scunthorpe United's game with MK Dons due to Scunthorpe's lack of fit goalkeepers. On 30 May 2013, Cutler joined Walsall after Scunthorpe's relegation to League Two. Cutler joined West Bromwich Albion as goalkeeping coach on 17 January 2018, after Albion were able to agree a compensatory fee with Cutler's former employers Walsall. In November 2018 Cutler was appointed goalkeeping coach at Aston Villa.
