[4] He made his first-team debut after coming on as a 75th-minute substitute for Ruud van Nistelrooy in a 5–2 win over Israeli side Maccabi Haifa in a UEFA Champions League group stage game at Old Trafford on 18 September 2002.

[5] He made his Premier League debut three days later, this time replacing Ryan Giggs with five minutes remaining of a 1–0 home victory over Tottenham Hotspur.

In May 2004, Pugh was traded to derby rivals Leeds United in part-exchange for Alan Smith, becoming the first player signed by manager Kevin Blackwell.

Pugh was sold to Championship rivals Preston North End in June 2006 for a fee of £250,000, becoming Paul Simpson's first signing as manager at Deepdale.

On 2 November 2007, Pugh joined Stoke City initially on loan with a view to a permanent move in January; manager Tony Pulis was "delighted to have signed a quality left-sided midfielder".

[21][22] He signed a new contract with Stoke whilst on loan at Preston, with Pulis remarking that Pugh was "an excellent professional... who can be relied upon to come in and do a good job if required".

[26] Pugh made six appearances at the start of the 2011–12 season and scored against Swiss side FC Thun the Europa League, giving Stoke a 1–0 win on 18 August.

[28] He left Stoke in January 2012 to rejoin Leeds United on a permanent transfer after five seasons with the "Potters", having made a total 89 appearances and scoring three goals for the club.

[36] In August 2012, Leeds manager Neil Warnock announced that Pugh and teammate Robbie Rogers had been placed on the transfer list to generate funds for a new striker.

[40][41] Pugh scored his first goal for Wednesday directly from a free kick in a 3–1 home victory over Brighton & Hove Albion on 2 February.

[42] He made his first appearance of the 2013–14 season on 9 November, as Leeds recorded a 4–2 victory at Charlton Athletic; Pugh won a penalty in the second half.

[46] He picked up an ankle injury which required surgery just two games into his Coventry career, and lost his first-team place at left-back to Ryan Haynes.

[53] Manager Gary Bowyer was reported to have signed Pugh to play in central midfield and to pass on experience to the younger players.

[60] On 30 March, he went from hero to villain on the cusp of half-time as he scored the opening goal before getting sent off during a crucial 2–1 victory over relegation rivals Chesterfield at Vale Park.

[65] Pugh became a full-time coach upon the expiry of his playing contract at the end of the season, though did take the #14 shirt and sat on the bench following a midfield injury crisis in September 2019.

[70] Club chairperson Carol Shanahan said that Pugh had been unlucky during his time in charge, missing Tom Pope and Devante Rodney to injury and having to self-isolate at home for two games.