Taylor, who is a lifelong Oldham fan, signed a professional contract with his hometown club, where a scout, Colin Shaw, scouted him and where he had been a trainee, on 1 August 2005. He made his debut for the club in a 3–0 home win over Nottingham Forest in the 2005–06 season, during which he made a further thirteen league appearances. In the 2006–07 season he made 51 appearances. On 3 March 2007, Taylor scored his first professional goal in a 1–1 draw with Carlisle United. After waiting 51 games for his first goal, Taylor then scored twice in a 4–0 demolition of Doncaster Rovers in his next game. He then made it four goals from three games with a goal against Leyton Orient in his next game. In April 2007 he signed a new three-year contract until summer 2010. On 2 June 2008, the Oldham Chronicle reported that Oldham had, the week before, rejected a bid for Taylor by Championship club Blackpool. Newly promoted Doncaster Rovers were also linked with a possible offer and it was claimed that Oldham had placed a £500,000 price tag on Taylor. Early in Oldham's 2008–09 campaign, Taylor scored a double in a 2–0 victory over Leeds United. Several weeks later on 20 September, he scored another double in a 3–3 draw with Hartlepool United. On 18 March 2009, he signed a new contract for Oldham, extending his contract with the club until 2012. After signing the deal Taylor told the club website: "Everyone knows Oldham is where I want to be, I love playing for this club. "There has always been speculation but all I want is to play for Oldham." His season was cut short, however, when he picked up an ankle injury during a morning training session on 21 April. On 26 April, Taylor was named to League One's Team of the Year, along with teammate Neal Eardley. On 8 June 2009, both the Oldham Chronicle and Yorkshire Evening Post reported that Leeds United were preparing to make a bid of over £500,000 for Taylor.
Millwall
On 31 May 2012, Taylor signed a one-year contract for Millwall on a Bosman free transfer from Oldham.
On 16 May 2013, it was revealed that Taylor would be signing for Blackburn Rovers at the end of his contract with Millwall. He signed on 1 July 2013. He made his debut in a 1–1 draw against Derby County coming as a 63-minute substitute for Joshua King, putting in a superb cross for Leon Best's equaliser. He scored his first goal for the club three days later in the League Cup against Carlisle United. Taylor scored both of Blackburn's goals in the FA Cup third round against Charlton Athletic, in a game that Blackburn went on to win 2–1. He also scored in the next round as Blackburn knocked out Premier League team Swansea City. Taylor's first league goal for Blackburn came in a 3–2 defeat to Brentford on 17 March 2015.
On 1 July 2016, upon the expiry of his Blackburn contract, he made the short move to join Bolton Wanderers on a Free Transfer, becoming Phil Parkinson's first signing since taking over as manager of the Wanderers. In January 2017, he rejoined Oldham Athletic on loan for the rest of the season, making 16 appearances before returning to his parent club. On 24 May 2018, Bolton confirmed that Taylor would leave the club on 30 June when his contract came to an end.
Blackpool
On 13 June 2018 Taylor signed a one-year contract with Blackpool.
In July 2019 Taylor went on trial with Bradford City. On 14 October he signed a short-term deal with Bradford City which would keep him at the club until the middle of January 2020. Bradford City manager Gary Bowyer admitted he was shocked that nobody had signed Taylor in the intervening period. However on 23 October, the deal fell through due to a registration problem stemming from Taylor playing in a FA Lancashire Cup match as a trialist for Barrow after the closure of the transfer window, which could result in a points deduction should he play for Bradford. Bowyer criticised the Football Association and English Football League for the mix-up. The deal was resurrected and completed on 11 November after Bradford were finally given full assurances that they would not face any sanctions for signing him, with Taylor signing an initial 2-month contract. Bowyer praised Taylor's versatility in November 2019.In December 2019 Taylor said he was keen to make up for the lost time. In January 2020 Taylor signed a contract extension with the club. Taylor left Bradford City on 13 May 2020 after his contract ended.
