Woodman spent the first five years of his career playing at Crystal Palace without making a first team appearance. In 1994, he moved to Exeter City making his debut at Lincoln City on the opening day of the season, but his time at St. James' Park was cut short following red cards in two successive matches. He was first sent off against Leyton Orient for violent conduct and then a week later for deliberate handball against Colchester United in the FA Cup. In both games, Woodman was replaced by 15-year old substitute Ross Bellotti, who remains the youngest goalkeeper ever to appear in the football league or FA Cup proper. Woodman moved to Northampton Town in March 1995 where he is regarded as something of a cult figure, being granted a testimonial by the club in summer 2007. He was loaned to Brentford in January 1999 and then moved there on a free transfer. After loans spells at Southend United and Colchester United in 2000, he signed permanently for Colchester United for the start of the 2001–02 season. Woodman found himself loaned out again, this time to Oxford United in January 2002, before signing permanently for them when the loan ended in March. Woodman was released by Oxford United in 2004 and then played for Stevenage Borough, Redbridge and Thurrock. His final match for Thurrock was a 2-4 Conference South play-off defeat against Eastbourne Borough on 3 May 2005. Woodman then briefly returned to the Football League with Rushden & Diamonds, making the final appearance of his career in a 1–2 defeat at Barnet on 29 October 2005.
Non-playing career
Coaching
In spring of 2006 he was appointed assistant manager at Rushden & Diamonds but left the club after they were relegated from the Football League at the end of that season to join his old teammate Alan Pardew at West Ham United as a coach. When Pardew moved to Charlton Athletic, Woodman followed him in the summer of 2007 as goalkeeping coach. In December 2010 he linked up with Pardew again at Newcastle United as goalkeeping coach and on 31 July 2015, he joined Crystal Palace in the same position to work under Pardew yet again. On 9 January 2017, following Pardew's departure and the appointment of Sam Allardyce as manager of Crystal Palace, it was announced that Woodman had left the club.
Woodman co-authored a book Woody & Nord: A Football Friendship with England managerGareth Southgate about their close friendship which grew from their time together as youth players at Crystal Palace, followed by their wildly differing fortunes in the professional game. Southgate's nickname Nord was coined by Wally Downes, who thought he sounded like Denis Norden. The book won the best sports autobiography category at the 2004 British Sports Book Awards.
Personal life
Woodman's son, Freddie, is a goalkeeper with Newcastle United. Southgate is Freddie's godfather.
