Club-record Bolton Wanderers transfer was a masterstroke - he was a second-tier cheat code | OneFootball

Bolton Wanderers have a long and tricky relationship with Dean Holdsworth, who went on to play quite well in the second-tier for the club.

Dean Holdsworth’s relationship with Bolton Wanderers is a complicated and long story to tell, but as a player, he put in some excellent performances and provided some special memories, as well as some extremely frustrating ones.

In the summer of 1997, Bolton were preparing for their first ever season in the new Reebok Stadium after their move from Burnden Park, and they were doing so on the back of romping to the second-tier title.

They won at St Mary’s against Southampton on the opening day of the campaign, but then went on to go winless in their nine matches, scoring just seven goals in the first seven matches of that run.

So, in early October, Wanderers broke their club-record transfer fee to bring in striker Dean Holdsworth for a fee believed to be in the region of £3.5 million from Wimbledon.

The Walthamstow-born attacker had scored well over 50 goals for both Brentford and Wimbledon before his move north, and he was viewed as a marquee addition for the club.

Having previously hit double figures in the top-flight for Wimbledon as recently 1995/96 campaign, just a couple of years after 17 and 19-goal campaigns, Holdsworth’s first season at Bolton, scoring three goals in 20 appearances, was a major disappointment as the Trotters were relegated, but the second-tier is where he began to spring to life.

Dean Holdsworth had his moments in the second-tier for Bolton

In the 1998/99 campaign, Wanderers finished sixth in the second-tier, with Holdsworth managing to hit 12 goals in the league, finishing up as their third top scorer behind Bob Taylor and Arnar Gunnlaugsson.

Under the management of Colin Todd, Wanderers played a very attacking style of football that suited their abundance of attackers, and Bolton began the season without a defeat in their opening 11 matches.

An average second-half to the season saw Wanderers slip away from the top two, and Holdsworth’s performances dipped too, before an injury curtailed his league campaign, with Bolton losing to Watford in the play-off final.

Upon his return in the 1999/00 season, there was a lot of change at the club in the early autumn with long-term boss Todd replaced by Sam Allardyce, and Wanderers again achieved a sixth-placed finish before a play-off semi-final loss to Ipswich Town, who they had beaten in the previous seasons’ semis.

Holdsworth improved upon his tally of 12 goals to notch 14 times in the league that season, finishing up as Bolton’s joint top scorer in the league alongside Eidur Gudjohnsen.

Wanderers had found themselves in a predicament that season, but they suffered just one defeat in their final 13 matches to finish sixth, with Holdsworth scoring a crucial goal on the final day to defeat Norwich City to clinch their play-off berth.

He then went on and scored three goals over their 7-3 aggregate loss to Ipswich in a controversial tie.

The 2000/01 season finally saw Bolton return to the top-flight, and Holdsworth again gave a more than adequate contribution to the cause, scoring 15 goals across all competitions and finishing up as their second top scorer behind Michael Ricketts.

Holdsworth had found himself on the fringes of the side as they fell short of a top two finish in the second-tier, but he again finished the campaign well with six goals in his final 11 games of the season.

Wanderers defeated West Bromwich Albion by five goals to two on aggregate in the semi-finals and then hammered Preston North End 3-0 at the Millennium Stadium, with Holdsworth failing to score, but he did start and play 89 minutes of that play-off final win.

Upon their return to the top-flight, Wanderers would embark upon a remarkable ride that saw them bring in some of the world’s genuine stars of the game, competing for top four finishes, reaching cup finals and going on European runs.

Holdsworth was not to be a part of that, with the step-up in quality seeing him eventually fazed out of the club by December 2002, after scoring just a couple of goals in 30 Premier League appearances back in the top-flight.

He did, though, enjoy a couple of famous moments in the top-flight with Bolton, as he scored the winning goal against Liverpool in their third game of the 2001/02 season, to make it three successive victories at the start of the campaign, following their promotion.

He also scored a crucial equaliser against Tottenham Hotspur, too, to help secure Bolton’s safety in mid-April.

Holdsworth was brought in to be Bolton’s potential point of difference in making them competitive in the top-flight, but he failed to do that, despite some special moments.

He did form part of a Wanderers era that saw them twice fail in the play-offs, before glorious success over local rivals, and he was always worthy of a double-figure contribution in terms of goals during that time.

One of his most memorable moments on the pitch, though, remains a sitter that he missed against Aston Villa in the semi-finals of the FA Cup at Wembley Stadium in 2000, with Bolton, the club who had won the first ever Wembley cup final in 1923, missing out on being at the last ever old Wembley cup final in 2000 as a result of that miss and then a subsequent 4-1 penalty shootout loss to the Villains in which Holdsworth missed again.

Then, off the pitch, Holdsworth fronted a takeover of the club in 2016 that saw him introduce Ken Anderson to the club, which eventually led to Bolton’s administration and the Trotters coming extremely close to liquidation – a moment in time in which they are now still recovering.

Holdsworth did a job, albeit not the job he was brought in for, but the former Wimbledon man did, generally, probably prove himself to be too good for the then First Division.