He was released by the club having made his first-team debut while on loan at Kidderminster Harriers and signed a short-term contract with Bury in 2006.

[11] He converted a Simon Heslop cross during a match against Dagenham & Redbridge to score his first career goal, which helped Kidderminster to a 3–1 victory.

[18][19] Bury were entangled in a relegation battle, and Pugh made his debut two days later after coming on as an 80th-minute substitute in a 2–1 home win over Rochdale.

[23][24] Pugh was a regular first-team player in 2006–07, playing particularly well in the first half of the season, and was offered an extended contract at the club in January 2007.

[32] Shrewsbury manager Gary Peters revealed that he had already attempted to sign him earlier in the season as part of a swap deal when striker Glynn Hurst moved to Bury.

[38] After struggling to feature in the team at the start of 2008–09,[39] Pugh joined fellow League Two club Luton Town on a one-month loan on 12 September 2008.

[40] His debut came in a 3–1 home win over Aldershot Town a day later,[41] after which manager Mick Harford said "He is an out and out winger, and he put in some good crosses.

[41] He was loaned out to League One team Hereford United on 26 March 2009,[43] and made his debut two days later in a 1–0 home loss to Huddersfield Town.

[52][53] Pugh signed for newly promoted League One club AFC Bournemouth on 4 June 2010 on a three-year contract, for a compensation fee.

[63] Bournemouth opened contract talks with him in December 2011,[64] and he opted to bide his time over the offer of a new three-and-a-half-year deal to concentrate on his playing performances.

[67] He was voted the Bournemouth Daily Echo Supporters' Player of the Year; this newspaper described him as "a rare shining light during an up-and-down campaign".

[70] He formed an effective partnership with fellow winger Ryan Fraser[77] as Bournemouth enjoyed their best start to a season in the second tier in 2013–14.

[78] In mid-November 2013 Pugh stated his belief that Bournemouth had made a "decent start" to the season; by this point he had scored 4 goals from 16 appearances.

[80] Pugh made 45 appearances and scored 5 goals in 2013–14[81] as Bournemouth finished in 10th place in the Championship,[82] which at the time was the highest league ranking in the club's history.

[83] In Bournemouth's first match of 2014–15, a 4–0 away win over Huddersfield on 9 August 2014, Pugh opened the scoring after only 26 seconds[84] with a composed finish from Matt Ritchie's cross.

[85] On 25 October 2014, Pugh played as Bournemouth beat Birmingham City 8–0 away to set a club record win,[86] in which he scored the first hat-trick of his career in the second half.

[5] Pugh and full-back Charlie Daniels formed a partnership on the left-hand side of the pitch during 2014–15, the duo starting all matches but one of a 14-match unbeaten run for Bournemouth.

[87] He scored the first goal in a 3–0 win over Bolton Wanderers on 27 April 2015 with a left-footed shot into the top corner; this result all but sealed Bournemouth's promotion into the Premier League.

[92] Pugh scored his first Premier League goal in Bournemouth's 4–3 away win over West Ham United on 22 August 2015,[93] with a curling shot past Darren Randolph in the 66th minute.

[108] He has been noted for his dribbling skills and his ability to get past opposition players, and in February 2015 was praised by manager Eddie Howe for adding "real intelligence with his movement".