Born in Goole, East Riding of Yorkshire, Featherstone came through Hull City's youth structure. He joined the Centre of Excellence at the age of eight and, along with Will Atkinson, James Bennett and Matty Plummer, penned a two-and-a-half-year professional deal with the club in December 2006. After starring for the youth and reserve teams, he made his first team debut against Burnley on 30 December 2006, coming on as a late substitute. He was one of the nominees for the 'Wickes Young Apprentice Trophy' in 2007. In September 2007 he signed a new contract to keep him at the club until June 2010, after a clause in his old contract stated that he would be offered a new one after making five first team appearances. During the 2007–08 season, Featherstone featured as a second-half substitute for Hull City against Chelsea in the third round of the League Cup. He played in the third round tie in the 2009–10 League Cup against Southend United. On 19 November 2009 Featherstone joined League Two outfit Grimsby Town on an initial month's loan. He made his debut in a 0–0 draw with Lincoln City on 21 November. He eventually made seven appearances for Grimsby, and eventually returned to Hull on 3 January 2010. He re-signed for Grimsby for a second loan spell on 11 January 2010. On 1 February 2010, Featherstone returned to Hull early having asked to have his loan contract cut short, down to the fact he had fallen out of contention at Grimsby, having made only one appearance for The Mariners in his second loan spell. During the 2010–11 season, despite being kept on at the club, Featherstone did not receive a squad number and eventually departed the club permanently in January 2011.
Hereford United
Featherstone joined League Two side Hereford United on an initial one-month loan on 4 November and signed a permanent deal to stay at Edgar Street in January. In May 2011 he signed a new one-year contract with the club. Following the conclusion of the 2011–12 season which saw Hereford relegated to the Conference National division, Featherstone seemingly departed United having failed to respond to the club's offer of a new contract.
Walsall
Featherstone signed with Football League One side Walsall on a one-year deal. He signed with The Saddlers on 6 August after impressing on trial with the West Midlands club.
Scunthorpe United
On 19 August 2014, it was announced that Featherstone had joined Football League One side Scunthorpe United on a "week to week" deal. He left the club on 2 September after his non-contract terms were cancelled.
Harrogate Town
On 3 October 2014, it was announced that Featherstone had joined Conference North side Harrogate Town.
Hartlepool United
On 31 October 2014, Featherstone returned to the Football League by signing with Hartlepool United on a short-term deal. Featherstone signed a new contract at the end of the 2019-20 season after an impressive season.
