[3] Even before he made his senior debut, he hit the headlines when he scored after just 38 seconds for England under 16s in a Victory Shield match against Northern Ireland.

[11] In September 2003, his manager George Burley issued a "hands-off" warning to teams trying to sign Holmes as well as fellow teenager Tom Huddlestone.

[12] Still aged 16, Holmes scored his first Derby goal in a 3–1 defeat to Coventry City on 25 October 2003 to become the club's youngest goalscorer.

[15] Holmes played three games for Derby at the start of the 2004–05 season and also appeared for England under 19s scoring in a 1–1 draw with the Czech Republic.

[20] Holmes played 15 league games for Swindon, winning the club's young player of the season award,[21] before returning to Derby County.

[25] Holmes again moved on loan at the start of the 2006–07 signing for Bradford City with full back Nathan Doyle.

[27] Holmes spent time on trial with Dutch side NAC Breda but remained at Derby without playing in a match during 2007.

Holmes returned to Derby at the end of the season, but the club decided not to renew his contract, and he was one of four players to be released.

[35] He was attracted by the promising youth set up under new coach Jan Poortvliet,[36] chairman Michael Wilde and the size of the club.

[39] Holmes started Southampton's opening seven games of the season, and scored a second goal, once again in the League Cup, but was injured in a 4–1 defeat to Queens Park Rangers in September.

[37] Southampton struggled without Holmes,[citation needed] who returned to action in a 2–0 defeat to another team fighting against relegation Nottingham Forest on 20 December 2008.

[42] As a result of the club's form Poortvliet resigned as manager and was replaced by his assistant Mark Wotte, in whose first game in charge, Holmes again went off injured.

[45] On 14 February 2012, Holmes signed a one-month loan deal at League Two side Oxford United, which made him available for their match against Dagenham and Redbridge at the Kassam Stadium.

[54] On 8 January Exeter played the first leg of their FA Cup match against Liverpool and on the stroke of half time, Holmes scored directly from a corner kick.