Bailey playing for Southend United
|Full name||Nicky Francis Bailey|
|Date of birth||10 June 1984|
|Place of birth||Putney, England|
|Height||5 ft 10 in (1.78 m)|
* Senior club appearances and goals counted for the domestic league only and correct as of 15:50, 7 May 2015 (UTC).
Bailey, born in Putney, London, began his career with local team Fulham but was released and moved to non-league Sutton United where he played as a teenager. At twenty, he went to Conference side Barnet in 2004 for a tribunal fee of £10,000.
Bailey was Paul Fairclough's first signing as Barnet manager, and he immediately established himself as a regular for the club.
Bailey made his Barnet debut against Farnborough Town in a 0–0 draw in the Football Conference on 17 August 2004, and scored his first goal for the club on 4 September 2004 in a 5–1 win against Morecambe. He helped the club to promotion in the 2004–05 season and then establish itself in Football League Two over the following two years. In 2006-7 he was voted Barnet FC Player of the Season by the clubs' supporters.
After attracting interest from several clubs during the January transfer window, it was announced on 29 June 2007 that Bailey was discussing terms with Southend United of League One. He eventually signed with Southend on 3 July 2007 for a fee of £175,000. After winning the club's player of the year award for the 2007–08 season, Bailey was transfer listed on 5 June 2008 after failing to agree to terms over a contract extension. He signed with Charlton Athletic on a three-year contract for a fee that could reach £750,000 in August 2008, seeking championship football and a higher wage, a move that has made him unpopular with Southend fans.
Charlton Athletic were relegated from the championship after finishing at the bottom of the table, despite Bailey finishing as top scorer. He was voted the club's player of the season.
On 26 April 2010 it was announced that Bailey was in the 2009–10 PFA team of the year alongside teammate Frazer Richardson. Bailey captained Charlton to a semi-final playoff defeat against Swindon Town, the semi-final went to penalties and it was Bailey who missed the decisive spot kick for Charlton to send Swindon through to the final. It was to be his last kick as a Charlton player.
On 19 June 2010 the BBC claimed that Middlesbrough F.C. were set to sign Bailey for a fee of £1.4m. The deal was confirmed by both clubs on 24 June 2010, and Bailey was officially announced as a Middlesbrough player on 8 July. Bailey had a difficult start as a Middlesbrough player, however under new manager Tony Mowbray, Bailey was converted to a more defensive minded midfielder and became popular with the fans. His ongoing impressive form led to Bailey being nominated for the Championship player of the month in December 2011.
Bailey scored his first goal for Middlesbrough against Burnley on 10 September 2011. Bailey then scored again in Middlesbrough's 2–1 home win against Southampton. Bailey scored on 21 August 2012, his third goal for Boro, again against Burnley in a 3–2 home win. Following injuries to Rhys Williams and Jonathan Woodgate, Bailey has captained Boro three times in the 2012–13 season. Bailey's fourth Boro goal was a spectacular long shot in a 2–1 home defeat to Leicester City. At the end of the 2012–13 season Bailey's contract expired.
Bailey joined Millwall on a two-year deal in July 2013. He suffered numerous injuries during his two years with the club, limiting him to 39 appearances. He was released at the end of the 2014–15 season following Milwall's relegation to League One.
Bailey was picked to play for the England C national team, by Paul Fairclough when he was also manager of Barnet. He made four appearances before moving into the Football League, which meant he could no longer take part.
- "Professional retain list & free transfers 2012/13" (PDF). The Football League. 18 May 2013. p. 74. Archived from the original (PDF) on 2 August 2014.
- Hugman, Barry J., ed. (2010). The PFA Footballers' Who's Who 2010–11. Edinburgh: Mainstream Publishing. p. 29. ISBN 978-1-84596-601-0.
- "Middlesbrough sign Nicky Bailey from Charlton Athletic". BBC Sport. 8 July 2010. Retrieved 8 July 2010.
- "Burnley 0 Boro 2". Middlesbrough F.C. 10 September 2011. Retrieved 10 September 2011.
- Nicky Bailey: Millwall sign ex Middlesbrough midfielder
- Millwall release 18 players including captain Alan Dunne
- Former Barnet favourite Nicky Bailey is training with the Bees with a view to a return to the club he left eight years ago
- Nicky Bailey: Barnet re-sign former Millwall midfielder
- Haines, Gary (13 August 2008). "Addicks seal midfielder deal". Charlton Athletic F.C. Retrieved 13 August 2008.