Bent then scored five goals in 29 games in 1997–98, as the Bees struggled in vain to avoid relegation under Eddie May and then his replacement Micky Adams.

With the club heading for administration,[5] he was sold on to First Division rivals Port Vale for £300,000 on 15 January 1999, as one of long-term manager John Rudge's last purchases.

He later described moving from Crystal Palace to Port Vale as "my dream blown up in my face" as he struggled to adapt to life outside London, referring to the culture shock he said "Someone said 'All right, Duck', which put me on my toes.

'[7] Bent became the Blades top scorer in 1999–2000 with 15 league goals in 32 appearances, including a hat-trick past West Bromwich Albion in a 6–0 thrashing at Bramall Lane on 19 February.

The club had struggled under Adrian Heath before finding an upturn in results after Neil Warnock stepped into the hot seat in December.

Former club Crystal Palace reportedly targeted him for a swap deal of Clinton Morrison and £1.5 million; however, manager Alan Smith denied that he had made any such offer.

[10] Bent scored his first goal for Rovers against bitter East Lancashire rivals Burnley in a 2–0 win at Turf Moor on 17 December 2000.

[11] He went on to hit 11 goals in 34 appearances in 2000–01, justifying Graeme Souness's fee, as the Ewood Park club won promotion back to the Premier League.

He stayed at Portman Road for the 2002–03 campaign, hitting 12 goals in 38 games, as the Tractor Boys missed out on the play-offs by one place and four points.

However, Ipswich entered administration and were forced to sell talent such as Marcus Stewart, Titus Bramble, and Darren Ambrose; a relegation battle was only avoided after manager George Burley was replaced by Joe Royle.

Bent joined newly promoted Premier League side Leicester City on loan for the 2003–04 campaign, in a move that reunited him with manager Micky Adams.

Bent scored ten goals in 35 games, though the First Division beckoned for the Foxes, as the Walkers Stadium club finished six points behind 17th place Everton.

Unable to afford his £17,000-per-week contract, in June 2004, Ipswich sold Bent to Everton for a fee of £450,000; the Toffees manager David Moyes said that "he's got athleticism, he's quick, good in the air".

Bent joined Wigan Athletic on Transfer Deadline Day (31 August 2007) on a season-long loan move, one of nine summer signings by boss Chris Hutchings.

He was still out of the first-team plans at St Andrew's; he again moved on loan in August 2010, as he joined Mick McCarthy's Premier League side Wolverhampton Wanderers until 4 January 2011.

[25] With the Blades in free-fall Bent made ten appearances, mainly from the bench, before returning early to Birmingham in mid-April having failed to score a goal.

[41] He was charged with affray and possession of a Class A drug in September 2015 after police used a taser whilst arresting him at his home in Esher, Surrey.

[43] In February 2016 he admitted to one charge of affray and possession of cocaine; he was given a suspended 12-month prison sentence, a two-month curfew and 200 hours of compulsory unpaid work.