Nicky Bailey joined The Hawks in the summer of 2019 from an impressive three-year spell at boyhood club Sutton United.
Bailey started his youth career at London side Fulham before joining Sutton United as a teenager. In 2001 he broke into the senior squad at The U’s he went on to make 85 appearances scoring a total of 27 goals before departing in 2004.
On the 17th August 2004, Bailey pulled on the Barnet shirt for his debut against Farnborough Town. Barnet was a great few years for Bailey as he enjoyed helping The Bee’s to a promotion into the football league in his first season. He was a key component in ensuring Barnet stayed in League Two for his remaining seasons at the club.
In 2007 League One teams began to notice the talent Bailey possessed and a move to Southend United followed for a fee of £175,000. He impressed in his first season with The Blues and achieved the Player of The Season award for Southend. However, his spell with the club came to an unfortunate ending as a disagreement over a new contract saw him leave in 2008.
Charlton Athletic was the next destination for Bailey where he signed a three-year contract. The chance to play Championship football was something he couldn’t turn down. Despite being a favourite with Charlton, the side were relegated after his first season. Bailey ended top scorer for The Addicks and was voted Player of The Season. He spent two years at The Valley making a total of 89 appearances.
In 2010 Middlesbrough acquired Bailey’s services for a reported fee of £1.4m. In a three-year spell at Boro he was converted into a defensive minded midfielder but still managed to bag himself four goals during his three years at the club against top class opposition in Southampton, Leicester City and Burnley.
After Bailey’s contract expired at Boro he joined Millwall in July 2013, however after a lengthy run of injuries he couldn’t show his true quality and was later released from the club following their relegation into League One.
He returned to Barnet for a brief spell making only a handful of appearances before moving back to Sutton United for his second spell at his former academy club. During his first season back with The U’s Bailey helped them win the National League South title.
In 2017 Bailey experienced a historic FA cup run with Sutton as they reached the FA cup fifth round for the first time in the club’s history, the run included a famous 1-0 victory over Leeds United. The U’s were drawn against Arsenal in the fifth round where they fell short in a 2-0 defeat.
In 2019 Bailey followed Sutton manager Paul Doswell for the 2019/20 season at Westleigh Park.