Stockport County As a youth, Bailey started his career at
non-League club
Nantwich Town scoring on his debut at Atherton Collieries in August 2002. He impressed
Stockport County of
the Football League enough to earn a trial for
The Hatters. Whilst on trial, he impressed manager
Carlton Palmer who offered Bailey a three-year contract, which Bailey duly signed. Under new manager
Sammy McIlroy, Bailey impressed in the
reserves and was sent out on a one-month loan to
League Two club
Scunthorpe United at the start of the
2004–2005 season, making his début against
Rochdale, a 3–1 defeat for Scunthorpe. He played in four first-team matches whilst at
Glanford Park without scoring. He returned to Stockport in October 2004 and his début under McIlroy in the 2–0 defeat against
Wrexham in the
Football League Trophy. McIlroy was sacked in late November and was replaced by
Chris Turner. Bailey made his league début under Turner in the
League One game against
Chesterfield as an 89th minute
substitute, replacing
Mark Robertson. Bailey was sent out on loan to
Conference National outfit
Northwich Victoria for a month, making his début at
Carlisle United, a 1–0 defeat for Northwich. He played in five first-team matches for Carlisle without scoring. He was released by Stockport in May 2005.
Crewe Alexandra Whilst on loan at Northwich Victoria, Bailey trained with
Championship club
Crewe Alexandra and scored twice in an under-18 game for
The Railwaymen. This performance impressed manager
Dario Gradi enough to earn him a one-year contract in May 2005. During the
2005–06 season, Bailey went out on loan to non-league clubs
Hereford United,
Southport and
Lancaster City to gain first-team experience, but despite not breaking into the first team during the season and Crewe's relegation to League One, he was offered a one-year contract extension. In the
2006–07 season, Bailey found himself in a similar situation to the previous season, failing to break into the first team and being sent out on loan, to
Barrow of the
Conference North, for whom he appeared in ten matches. He was offered another one-year extension to his contract. Bailey made his Alexandra début on 1 September 2007 in a 1–1 draw at
Swindon Town, replacing
Tom Pope in the 82nd minute.
Change of position Bailey did not impress manager Dario Gradi as a
striker. Gradi, who had trained the likes of
David Platt and
Dean Ashton in their early years, announced his intention to convert Bailey from a striker to a
centre back. Gradi did not expect Bailey to push through and challenge as a first team centre back until the start of 2008. Bailey made his full debut for Alexandra away at
Oldham Athletic in the second round of the
FA Cup, where he played at centre back. Bailey went on loan to
Weymouth for a month in March 2008; he made four appearances without scoring. When he returned to Crewe, Bailey did not feature in the team and he was released in May 2008; he played only times for Crewe.
Later career Bailey rejoined Northwich Victoria in May 2008. He was loaned to
Hinckley United in December 2008, scoring on his debut for the
Conference North club. He joined
AFC Telford United in August 2013. Shortly afterwards, he was sent on loan to
Nantwich Town. ==References==