He played for the club in their 2010 FA Cup final defeat to Chelsea, but could not prevent them from being relegated out of the top-flight that same year.

He signed with Port Vale in July 2014 and also took on a coaching role with them before becoming assistant manager to Bruno Ribeiro in June 2016.

[9] He went on to feature as the "Citizens" main back-up player, making 16 Premier League starts and five substitute appearances during the 1995–96 relegation season.

He began the 1996–97 season as a first-team regular under manager Alan Ball after midfielder Garry Flitcroft had left the club.

He was instead loaned out to his home town club Hartlepool United in March 1997 and featured in six Third Division matches at Victoria Park under Mick Tait's stewardship.

Brown worked his way back into the "Sky Blues" starting eleven midway through the 1997–98 season and scored his first goal for the club in the FA Cup on 3 January in a 2–0 win over Bradford City.

[11] However, Joe Royle never utilised Brown in the First Division, and he was instead loaned out to divisional rivals Portsmouth in November 1999, who were then managed by his former City boss Alan Ball.

He made 40 appearances during the 2000–01 campaign and scored against Steel City rivals Sheffield Wednesday in a 2–1 League Cup defeat at Hillsborough on 1 November.

Brown heavily featured in the Battle of Bramall Lane; he limped off the field with an injury on 79 minutes leaving the game desperately short of players, and two minutes after he left the field another injury left United with only six players, forcing the game to be abandoned.

He scored 22 goals in 54 appearances in the 2002–03 season and was named on the PFA Team of the Year alongside midfield partner Michael Tonge as they helped United to finish third in the First Division.

Although well appreciated by fans for his hard work and honest contribution, the strengthening of the Spurs midfield under Martin Jol threatened Brown's position in the team with signings like Edgar Davids, Hossam Ghaly and Danny Murphy adding competition for places with Michael Carrick and Jermaine Jenas already at the club.

[31] On 15 May, Brown was in the Portsmouth side that lost 1–0 to Chelsea in the FA Cup final after a 59th minute Didier Drogba goal.

On 16 October 2010, Brown scored the winning goal in a 3–2 home win over Watford and remained almost ever-present for Portsmouth throughout the following months until both he and "Pompey" teammate Richard Hughes reached the stage where they would both be entitled to new contracts with increased wages which the club could not afford (Brown was reportedly paid £25,000 a week) if they played another game.

[34] Brown played 24 times and scored three goals for Portsmouth during the 2010–11 season, with his last game before the contract cause would have been activated coming on 26 December 2010.

[40] After missing some games with a calf injury, Brown returned to the starting line-up at Elland Road against Crystal Palace on 10 September.

[43] During the pre-match warm-up for Leeds' FA Cup game against Arsenal at the Emirates Stadium, Brown kicked a ball into the face of pundit Martin Keown who was doing punditry pitch-side with Robbie Savage for ESPN's coverage of the game – he claimed that he had in fact been aiming for Savage.

[44] He endured numerous spells out of the first-team until manager Simon Grayson was replaced by his former Sheffield United boss Neil Warnock in February 2012.

[51] Brown signed a one-year contract with League One club Port Vale in July 2014; manager Micky Adams also gave him the responsibility of coaching the reserve team.

[52] He scored the only goal of the game on 15 November, helping the "Valiants" to a 1–0 win over Rochdale at Vale Park;[53] his performance in the match earned him a place on the Football League Team of the Week.

[55] Despite his age he proved a key first-team player, scoring six goals in 39 appearances in the 2014–15 campaign,[56] and had to focus his time on playing rather than coaching.

[59] In May 2016, chairman Norman Smurthwaite announced that Brown would assist him in appointing a successor to departing manager Rob Page.

[65][66] Bruno Ribeiro resigned as manager of Port Vale on 26 December 2016, and Brown was placed in temporary charge.

[68] In the January transfer window he was forced to sell goalkeeper Jak Alnwick and reigning Player of the Year Anthony Grant, whilst top-scorer Alex Jones's loan deal expired and six other players left the club; Brown brought in youngsters Callum Guy, Tyler Walker, Olamide Shodipo, Axel Prohouly and Leo Fasan on loan, and signed Scott Tanser, Chris Eagles and Danny Pugh on free transfers.

[69] However, his team were dogged by injury problems, and Brown told the media that if he could keep the Vale out of the relegation zone that would be an achievement "off the scale".

[74] His first summer signing was former two-time Player of the Year Tom Pope on a free transfer after he managed to secure his release from Bury.

[75] He went on to sign ten more players during the window: goalkeepers Rob Lainton and Sam Hornby, defenders Joe Davis, Antony Kay, Gavin Gunning, Lawrie Wilson and Graham Kelly, midfielders Michael Tonge, Cristian Montaño, David Worrall and Harry Middleton, and striker Tyrone Barnett; he also signed youngsters Rekeil Pyke, Marcus Harness, Tyler Denton, Ben Whitfield, Jack Stobbs and Tom Anderson on loan.