Hull City Born in
Goole, Humberside, Featherstone came through
Hull City's youth structure. He joined the
Centre of Excellence at the age of eight and, 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. The following day, Featherstone made his debut in a 2–2 draw with
Newport County. On 2 February 2015, Featherstone extended his contract until the end of the
season. On 25 June 2015, Featherstone signed a new deal with Hartlepool. On 27 August 2016, he scored his first goal for Hartlepool in another 2–2 draw with
Newport County. On 7 March 2020, he made his 250th appearance for Hartlepool in a 1–0 home defeat to
Ebbsfleet United. Featherstone signed a new contract at the end of the
2019–20 season after an impressive campaign. In the
2020–21 campaign, Featherstone played an integral role in central midfield and formed a strong relationship with
Mark Shelton and
Gavan Holohan in midfield as Hartlepool qualified for the play-offs in 4th place. In the play-off eliminator against
Bromley, Featherstone played an excellent long ball through to
Rhys Oates to open the scoring for Pools in a 3–2 win. In the
2021 National League play-off final, Featherstone started in the final but missed a penalty in the shootout. However, Hartlepool prevailed 5–4 on penalties and were promoted back to the Football League. Featherstone lifted the play-off trophy alongside club captain
Ryan Donaldson. Following Hartlepool's promotion back to
League Two, Featherstone was announced as Hartlepool's new club captain and signed a new two-year contract. In the 2022–23 season, he moved into the top ten most appearances list for Hartlepool United. Following Hartlepool's relegation to the National League at the end of the season, Featherstone left the club on 28 July 2023 having made 380 appearances. Following Featherstone's departure, manager
John Askey said: "I may have only worked with Nicky for a few months but I know he will remembered as a club legend. A great player who offered me great support during last season and I can't thank him enough for his contributions." On 3 November 2023, Featherstone extended his contract until the end of the 2023–24 season; he was also granted a testimonial match to celebrate his ten seasons of service to the club. During the season, he regained the captaincy from
David Ferguson. At the end of the season, he was offered a new deal with the club. On 9 May 2024, Featherstone signed a dual contract as a player-coach at Hartlepool. Early in the 2024–25 season, Featherstone entered the top five appearance makers for Hartlepool describing it as "a very proud achievement". On 7 September 2024, Featherstone made his 400th start for the club in a 0–0 home draw with
FC Halifax Town. On 14 December 2024, he made his 600th career appearance in a 0–0 away draw with
Southend United. On 26 July 2025, Featherstone's testimonial took place with Hartlepool defeating a
Leeds United XI 3–0 at
Victoria Park. ==Managerial career==