A promising youngster from the academy, Bailey made his first team break through in the 07-08 season making numerous appearances on the substitutes bench before getting his first run out in red away at Doncaster in December 2007.
The following season prove to be Bailey's real break through year. After a impressive summer he played much of the first half of the season under Steve Holland and Dario. Making over 30 appearances in all he had really established himself as a first teamer.
A knee injury at the beginning of 2009 saw a real struggle to break into the side during Gudjon Thordarson's reign, Bailey made just one start in the 09-10 season before Thordarson was sacked.
He was re-instated to the midfield instantly upon Dario's return as manager though injury has seen a stop start season up to mid-March for the defensive midfielder.
|Match highlights - Pompey 5-1 Barnet
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|The Sunday Inquest - Hartlepool
» Plymouth : 25/09/2016 10:49:01
|The Opposition View - Carlisle United
» Wycombe : 25/09/2016 09:15:01
|DRFC Ferguson - We Are Just Not Ruthless Enough
» Doncaster : 25/09/2016 09:00:01
|Rovers Beaten At Luton
» Doncaster : 25/09/2016 08:00:00