Southend United

Webb started his career as a trainee at Southampton but failed to break into the Saints' first team squad.^[2] In December 2000, Webb was brought to Southend United for a fee of £10,000 by his father David, who had recently taken over as manager of Southend in September. Webb went on to make 39 appearances for the Shrimpers between 2000 and 2002, scoring four goals, but found his first team opportunities limited after his father's resignation in October 2001, following which Daniel had two loan spells at Brighton & Hove Albion in 2001–02 and 2002–03, where he made a total 16 appearances and scored one goal against Notts County,^[3] however a permanent move failed to materialise.^[4]

Hull City

In 2002 Webb left Southend, moving to Hull City on a free transfer, where he went on to make a total of 18 appearances, scoring one goal, between 2002 and 2004. However, Webb always had a bit-part role at Hull and was loaned out to Lincoln City in his first season at the club, where he scored once against Bristol Rovers.^[5] Webb returned to Hull making a handful of first team starts at the beginning of the 2003–04 season, which earned him a Division Three runners-up medal. He scored his only goal for the club in a Football League Trophy tie against Scunthorpe United in November 2003.^[6] His first team opportunities became limited in the second half of the season and he was sent out to Cambridge United on an initial one-month loan.

Cambridge United

Webb impressed while on loan at Cambridge,^[7] securing another month's extension to his loan.^[8] In total he made 10 starts and scored one goal while on loan at the U's. In February 2004, Cambridge made the move permanent,^[9] and Webb went on to make a further 35 appearances and scored three goals for the club. The player's time at the club was not without controversy and in August 2004, Webb was fined by United's manager Hervé Renard for an on-the-field punch-up with teammate Luke Guttridge during a match against Shrewsbury Town.^[10] Webb was released by Cambridge at the end of the 2004–05 season after the club's relegation from the Football League and severe financial difficulties.^[11]

Yeovil Town

Webb started the 2005–06 season with Weymouth; however, in January 2006, he moved to Yeovil Town,^[12] teaming up once again with his father who had bought into the club in December 2005. David Webb's executive role however was brief, ending in February 2006, and his son never really subsequently broke into the first team, making only 10 appearances in 18 months at the club. In 2007, Webb was again loaned out repeatedly with brief spells at Rushden & Diamonds and with Woking, where a strong performance in his debut against Aldershot Town, in which he scored with his first touch,^[13] brought him to the attention of Terry Brown, the then Aldershot manager, who was later to sign him for Wimbledon.

Marsaxlokk

Having been released by Yeovil at the end of the 2006–07 season,^[14] Webb moved to Malta to sign for champions Marsaxlokk under the guidance of English manager Brian Talbot.

Webb only played once for Marsaxlokk in an appearance in a Champions League qualifier against FK Sarajevo.^[15]

AFC Wimbledon

Following his stint with Marsaxlokk, Webb returned to England to sign for AFC Wimbledon on 23 July 2007,^[16] ending the club's long search for a "target man".^[17][18] However, Webb failed to score regularly for the Dons and after losing his place in the starting team played only a bit-part role for much of the second half of the 2007–08 season. He was one of eight players released at the end of the campaign after being deemed surplus to requirements by Dons boss Terry Brown.^[19]

Chelmsford City

On 1 July 2008, he signed a contract with Chelmsford City becoming the Claret's second pre-season signing. However was later released by Chelmsford City for not being in Jeff King's plans.

Havant & Waterlooville

After being released by Chelmsford City, he signed a contract with Havant & Waterlooville in October 2008.^[20] He made three league appearances for Havant before going on trial at Salisbury City.

Salisbury City

Whilst on trial, Webb played one game and impressed manager Nick Holmes which resulted in him being signed by the club after they lost some of their first choice strikers due to financial problems. In 2009–10, Webb was a utility player for Salisbury, playing in defence, and once filling in for James Bittner in goal, against former club AFC Wimbledon, after Bittner saw red early in the second half.^[21] For a period of time, he also partnered Tubbs up front when other forwards in the squad were sidelined by injury.

Bath City

Webb left Salisbury City for Bath City during the summer of 2010. This was as a result of the club's two league demotion. He scored his first goal for Bath in their 2–1 defeat of Crawley Town and was soon a regular in the Bath side. However, after the summer break, Webb had trouble in breaking back into the side for the 2011–12 season and so joined his former club Salisbury City on loan on 2 November 2011.^[22] The loan move was later made permanent.

Leyton Orient

Webb joined Leyton Orient in 2011 as Under 14's coach. Since then he has progressed through the age groups and led the under-16s to National Category Three Cup final victory in 2014. Webb stepped up to assist Academy Director Andy Edwards at the start of 2015–16 season with the under-18s. After Edwards was promoted to assist manager Kevin Nolan on a more regular basis, Webb led Orient's youngsters to the Merit League Two title — finishing unbeaten from their 10 games.^[23]

On 1 July 2016, Webb was promoted to First Team Coach.^[23] On 29 January 2017, he was appointed manager at Orient after Andy Edwards resigned to take a role on the FA's coaching staff.^[24] On 30 March 2017, after 12 games in charge Webb resigned as manager of Leyton Orient.^[25] On 1 July 2017, Webb returned to Leyton Orient as Youth Team Coach.^[26] Webb later became a First Team Coach under Justin Edinburgh and became assistant to Ross Embleton after Edinburgh's death. Webb left the club by mutual consent on 12 February 2020.

Chesterfield

Webb became First Team Coach at Chesterfield on 24 April 2021.^[27] He became assistant manager in the summer, and had a spell as caretaker manager when manager James Rowe was suspended after allegations of misconduct.^[28][29] After Rowe left the club, Webb remained at the club under new manager Paul Cook.^[30][31]