[4] During the season, Chester City had a bid for the player rejected and Taylor spent time on trial with Nottingham Forest.
[4] After several weeks of talks in the summer of 2008, Taylor joined Chester on 1 July on a six-month loan deal with a view to a permanent signing.
[6] Taylor made his Chester debut as a substitute in a 6–0 defeat at Dagenham & Redbridge on 9 August 2008, which was also his first Football League appearance.
[7] Despite Chester not wanting his services, Vauxhall Motors insisted City were legally bound to pay for his transfer in January 2009.
[12] On 28 August 2012, Taylor, along with teammate George Boyd, were the subject of an undisclosed bid from fellow Championship side, Ipswich Town, which was accepted by the club.
[citation needed] On 30 August 2012, Ipswich returned with a second undisclosed bid of an initial £1.5 million, this time for Taylor only, which was also accepted by Peterborough.
[citation needed] On 14 June 2013, Taylor pleaded guilty to a charge of assault occasioning actual bodily harm.
[13] In April 2014, Ipswich manager Mick McCarthy confirmed that Taylor had been placed on the transfer list along with out of favour Goalkeeper Scott Loach.