Taylor started his footballing career at Tranmere Rovers as a youth team player since the age of 10. He joined Colwyn Bay on loan in 2009, where he made a total of 14 appearances. Whilst on loan with Colwyn Bay, Taylor scored a hat-trick in their 4–1 win over Lancaster City in the Northern Premier League Division One North in March 2009. Taylor made his first team debut in a League One match against Scunthorpe United in the 1–1 away draw on 2 May 2009, replacing Antony Kay as a substitute in the 89th minute. Taylor scored his first goal for Tranmere at Leyton Orient in the FA Cup First Round in November 2009. His first league goal came shortly after on 1 December 2009, in the 3–3 draw at Huddersfield. He won the "Young Player of The Season" award for the 2009–10 season. The club offered him contract terms for the 2012–13 season which he agreed, signing on for another year.