Redmond joined Wigan Athletic after being released by Everton in 2009.[2] It was later explained that Redmond was released by Everton because he was too small.[3] On 8 January 2011, he made his debut for Wigan, replacing James McArthur in the 80th minute of the FA Cupthird round win at Hull City.[4]
On 8 February 2014, Redmond joined Carlisle United on a one-month loan.[15] On 10 March 2014, he extended his loan spell with the Cumbrians for a further month until 5 April 2014.[16] At the end of the season, Redmond was offered a new deal by Wigan, but he turned the offer down.[17]
Hamilton Academical
Redmond signed a two-year contract with Hamilton Academical in June 2014.[18] Upon making the move, Redmond revealed he turned down a big money contract from Wigan, in an effort to kick start his career.[19]
He made his second debut for the club on 2 August 2014, as Hamilton beat Arbroath 2–1 in the Scottish League Cup.[20] He scored his first league goal of the season against Partick Thistle in a 3–3 draw on 1 November 2014.[21] Redmond said his first Hamilton goal since his return was "a long time coming" following his goal drought.[22] Redmond scored his first goal of 2015, in a 5–0 win over rivalsMotherwell.[23] However, Redmond ended his first season at Hamilton Academical with 27 appearances and two goals in all competitions after suffering a knee injury that ruled him out for the entire season.[24]
He was one of seven first-team players released by Hamilton at the end of the 2017–18 season.[25]
The New Saints
After leaving Hamilton, Redmond signed for Welsh club The New Saints in May 2018.[26]