Nicky Bailey

Southend United

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

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 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 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.

Millwall

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 Millwall's relegation to League One.

Barnet

Bailey started training with Barnet in October 2015, and re-signed on a short-term deal later in the month. On 23 December, Bailey was released after only four appearances.

Sutton United

At the end of his contract with Barnet, Bailey re-signed for Sutton United, initially until the end of the 2015–16 season. In his second spell at Sutton, Bailey made his first league appearance in a 2–0 away victory against Chelmsford City on 30 January 2016. He made a total of nine full and seven substitute appearances for the U's, helping them win the National League South title.

Bailey agreed to stay with Sutton for the 2016–17 season, playing in the National League, and scored the first goal in his new spell at the club by converting a penalty against Forest Green Rovers at The New Lawn on 9 August 2016, a game which ended in a 1–1 draw. After a string of impressive performances, Sutton supporters unofficially voted Bailey player of the month for August. Having converted two further penalties, one in a victory over Torquay United on 16 August and the other a consolation in a 2–1 defeat to Braintree Town on 13 September, Bailey scored his first goal for Sutton from open play on 8 October when he finished a corner supplied by Ross Stearn in a 4–1 rout of Surrey rivals Woking at Gander Green Lane. On 19 October 2016, it was announced that Bailey had signed a one-year contract extension with Sutton United and will stay with the club until the end of the 2017–18 season.

Bailey appeared for Sutton during their historic run to the 5th round of the FA Cup for the first time ever, including a 1–0 victory over Championship club Leeds United on 29 January 2017 and 0–2 defeat to Premier League club Arsenal on 20 February, where he made more tackles and interceptions than any other player.

On 4 March, Bailey was instrumental in helping Sutton to secure their first away clean sheet back in the non-League top flight, a 0–0 draw at Barrow, since a 9–0 away victory against Gateshead on 22 September 1990. Bailey featured the following day in The Non-League Paper's team of the day. Across three and a half seasons, Bailey played 125 times for Sutton in his second spell, scoring nine goals.

Later career Bailey followed Sutton manager Paul Doswell to Havant & Waterlooville for the 2019–20 season. He joined Gosport Borough on 19 September 2020. In September 2021 he joined Cray Wanderers.

International career 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.

Career statistics

Honours Barnet Conference National: 2004–05