While a talented and prolific goalscorer, Collymore's career was often marred by controversy, including his public struggles with mental health, outbursts on the pitch and arguments with coaches and teammates.

Collymore would remain with Palace for nearly two years, but struggled to find a place in the first team ahead of the prolific goalscoring partnership of Mark Bright and Ian Wright, and left the club in November 1992.

Collymore joined First Division strugglers Southend United for £150,000 on 20 November 1992, as the club was stuck firmly in the second tier relegation battle with the likes of Birmingham, Oxford and Peterborough.

"[7] Collymore's work at Southend attracted attention from a number of different teams, including boyhood club Aston Villa of the Premiership and newly relegated Nottingham Forest.

This was realised on 30 April 1994, when a last minute winner from Collymore saw Forest beat Peterborough United 3–2, securing a second place finish and automatic promotion to English football's top flight.

[12] Midway through the season, his impressive goalscoring record had attracted attention from Manchester United, who were looking to replace ageing striker Mark Hughes with a younger talent.

Collymore spent almost the entirety of late 1994 linked with a move to Old Trafford, with himself and Newcastle United's Andy Cole named as Sir Alex Ferguson's most wanted targets.

Eventually, Cole was signed by United for an English transfer record deal worth £7 million, while Collymore stayed at Forest for the remainder of the season; by the end of the campaign, however, he had received offers from Liverpool, Everton and Newcastle, with all three battling to earn his signature in the summer of 1995.

[13][14][5] Roy Evans would sign the deal to bring Collymore to Liverpool on 3 July 1995 for £8.5 million, shattering the English transfer record set earlier in the year by Andy Cole's move to Manchester United.

The up front pairing of Collymore and Fowler proved to be successful, as they scored a combined 55 goals in 1995–96 and established Evans' Liverpool side as serious contenders for that year's Premiership trophy.

Collymore watched from the sidelines as Eric Cantona fired home the winning goal with five minutes left on the clock, consigning Liverpool to another year with no major silverware.

Roy Evans' exciting young squad led the league for much of the first half of the season, but a series of poor performances in early 1997 saw them fall behind winners Manchester United and eventually finish 4th.

[16] Collymore was again a regular fixture in the attack and was a consistent goalscorer and creator, but became the subject of increasing media scrutiny throughout the season, as tabloids accused him and most of his teammates of being unprofessional, with the squad being dubbed the "Spice Boys" by newspapers in 1997.

During a match against Liverpool on 28 February 1998, Collymore accused former teammate Steve Harkness of racist abuse, an incident that was later picked up by the Professional Footballer's Association (PFA), but went unresolved and was closed after both players met in private and agreed to move on without charges.

[28][29] After a summer move to Greek side Panathinaikos failed to materialise, Collymore was sent out on a three month loan to Fulham at the start of the 1999–2000 season, with an option for the club to sign him for £1 million at the end.

[30][18] Collymore and Aston Villa mutually agreed to separate after he returned from his loan spell at Fulham, and he spent the rest of 1999 training with the youth team and looking for a new club.

[36] Having fully recovered, Collymore remained with Leicester through the summer transfer window and was thought to be the club's new first choice striker after Emile Heskey had left for Liverpool in the summer; however, with Martin O'Neill having departed Leicester to manage Celtic, he was dropped by replacement manager Peter Taylor in favour of new signing Ade Akinbiyi and instead often brought on as a midfield substitute.

[42] He would later retract this request, but manager Peter Taylor still placed him on the transfer list, citing Collymore's poor fitness, lack of commitment and attitude problems.

[43][44] Having fallen out of favour with another manager, and demoted to the reserve squad, where he was involved in a half time altercation with teammate Trevor Benjamin,[45][46] Collymore and Leicester would eventually agree to part ways, and he was allowed to leave on a free transfer in October 2000.

[12][43] Collymore was immediately signed by longtime admirers Bradford City on 26 October 2000, a move described as "desperate" by BBC Sport pundit Mark Lawrenson.

VFB Stuttgart and Celtic both made offers for Collymore, but he would eventually choose to sign with Spanish outfit Real Oviedo after just 8 games and 10 weeks with Bradford.

[59] He was again brought on during the second half of his home debut a week later in a loss against Villarreal, but was dropped by coach Radomir Antić after the game and told to improve his fitness.

[72] He also worked as a commentator for BT Sport, he was released from his contract in 2015 for criticising their lack of action regarding sectarian chanting during a game between Rangers and Raith Rovers.

[76] In October, Collymore, Martin, Lawrence and director Gary Lockett formed a panel to appoint a new club manager following the sacking of Phil Brown.

[84] In early 1998, Collymore was accused of assault by the mother of his child, Michelle Green; she alleged he had punched her in the face and caused injury after an argument regarding their son on 22 December 1997.