Nicky Francis Bailey (born 10 June 1984) is an English retired professional footballer who played as a midfielder.

Bailey, born in Putney, London,[2] began his career with local team Fulham but was released and moved to non-league Sutton United where he played as a teenager.

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.

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.

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.

[13] 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.

[15] 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.

[16] 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.

[18][19] 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.