As the clock ticked past 11 o'clock and the January transfer window slammed shut, fans were finally able to take stock of the business done by their club, and work out what could possibly lie ahead for them in the next few months of the season.

Some were very busy on deadline day with Middlesbrough signing three players including goal-machine Jordan Rhodes, in a big-money deal from Blackburn.

Others, such as Bolton Wanderers, Nottingham Forest, Cardiff City and Fulham were unable to bring anyone in permanently due to their transfer embargoes.

We have looked at the transfer activity of all 24 Championship clubs and come up with the FIVE teams that have endured the worst January transfer window......

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PRESS THE IMAGE BELOW TO SEE THE 5 CLUBS!

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Bolton Wanderers

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Poor Bolton. With the club bottom of the Championship with only three wins all season and £179.2m in debt things couldn't get much worse for Neil Lennon's men.

Due to their sorry financial state, the club were also not allowed to purchase any players - if anything, they needed to sell players to try and ease the wage bill at the administration-threatened club.

Amazingly enough, key players such as Zack Clough and Mark Davies, who were rumoured to be part of the Macron exodus during the transfer window ended up staying and fans will no doubt be looking towards them to secure an unlikely survival.

In some ways this could be viewed as a positive, and if the club do stay up then this transfer window will undoubtedly have been a success.

However if the Trotters do fall through the trap door, they will be in an even more sorry financial state, and the money that could have been raised from selling the duo in January might prove pivotal in Bolton's success.

Neil Lennon was also forced to give up veteran Shola Ameobi as the club just simply couldn't afford to offer the journeyman striker a new contract.

With Bolton needing as much firepower as possible to dig themselves out of their hole, his goalscoring prowess will certainly be missed in the attacking line-up.

Bristol City

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It was a case of close, but not quite close enough for the Robins in this transfer window as they came within inches of signing two proven goal-scorers only for the moves to be rebuffed, leaving Bristol City fans frustrated.

On deadline day the club reportedly had a bid accepted for Walsall striker Tom Bradshaw only for Walsall to publicly declare that the player was not for sale.

Before that, the Robins reportedly had a bid accepted for Bolton's young striker Zach Clough, only for the move to later fizzle out.

The club were also served more frustration on deadline day as they had a £2m bid rejected for sought after Gillingham star Bradley Dack.

Bristol City's return to the Championship has been anything but an easy ride and with the club sacking Steve Cotterill halfway through January's transfer window it was up to the inexperienced interim manager John Pemberton to try and give the club some direction.

However with the club seemingly in a relegation battle, it seems that many stars weren't willing to make the move to a club which could be in the third division next season.

One positive bit of news was the surprise return of Scott Golbourne, who joined from Wolves for £300,000 but fans will be left wondering if they'll have enough goalscorers to stay in the Championship for another season.

Wolves

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It was probably inevitable that Wolves were going to lose their star striker Benik Afobe at some point, and when Bournemouth came calling the writing was on the wall for Kenny Jackett's side.

With the club in a state of financial limbo due to owner Steve Morgan's decision to want to sell up, a £10m bid from a Premier League team for their prized asset was just too good to turn down.

With the deal completed early on in the window, Kenny Jackett had over two weeks to find a suitable replacement for the England under-21 star.

Unfortunately despite being linked to a number of strikers, fans were left underwhelmed when Joe Mason arrived at Molineux to fill the hole left by Afobe.

The £3m rated 24-year-old hadn't been an out and out goalscorer at Cardiff and with £10m in the kitty, fans were hoping for a much bigger name to score goals for the club.

The side, currently in 12th position in the Championship after an inconsistent campaign, were linked with a deadline day swoop for Boro's Kike, but the Spaniard ended up staying at the Riverside.

The club also lost left-back Scott Golbourne who surprisingly departed to Bristol City after falling down the pecking order at Molineux.

With his departure confirmed, Wolves were only left with one left-back in the squad - Sylvain Deslandes, who hasn't played a league game for the Midlands side.

Fans were hoping that the club might pull their finger out to sign another left-back but nothing came to fruition despite some reports that the club might make a move for West Brom left-back Sebastien Pocognoli.

Wolves' acquisition of Mike Williamson on loan until the end of season was one highlight of an otherwise disappointing transfer window in which the club failed to live up to the fans' expectations.

Cardiff City

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Cardiff are another club feeling the pinch and were forced to go under a transfer embargo midway through the January transfer window after breaching the Football League’s Financial Fair Play regulations.

Russell Slade's side haven't had a bad season to date with the cap-wearing boss steering the Bluebirds to 9th position after 29 games - just three points off the play-off places.

However with clubs around them being able to make permanent acquisitions to improve their squads, Cardiff were forced to change their strategy after being hit by the embargo.

The Bluebirds boss managed to bring in Lex Immers on loan but that was all the business that the Welsh side conducted, with even Slade admitting that Immers probably wouldn't have signed if the club had been in a better financial state.

Slade was also keen to keep Tony Watt in Wales for the remainder of the campaign by signing him on a permanent deal but due to the restrictions placed on them this proved to be impossible so he returned to parent club Charlton.

Cardiff were also unable to keep hold of some of their assets as Joe Mason sealed a transfer to rivals Wolves - a deal which angered and confused former player Mark Hudson.

Alex Revell, who admittedly had only scored 3 goals in a year for the Bluebirds, also left for MK Dons on a free transfer, as well as big earner Kenwyne Jones, who left for UAE side Al Jazira.

However, getting youngster Tom Lawrence in on loan from Leicester City on deadline day was a smart acquisition after he impressed at Blackburn in the first half of the season.

Cardiff have almost certainly been impeded by the embargo which scuppered any chances to make valuable reinforcements to their squad and the fans will definitely be left wondering what could have been if they fall short in the race for the play-offs.

Leeds United

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Although this year's transfer window didn't spark as much outrage as last year's when the club sold two players in the final few minutes before the deadline, it was still a disappointing month for Leeds United fans with little money spent on improving the squad.

Losing Sam Byram to West Ham was a big loss for the Yorkshire side. Like Afobe's move to Bournemouth, it was inevitable, and was going to happen sooner rather than later due to the inescapable lure of Premier League.

Leeds received £4m for the talented youngster but only spent a fraction of that money on players with Toumani Diagouraga the only notable signing to be introduced to the Elland Road faithful.

The former Brentford man made an instant impact with a goal on his debut against Bolton in the FA Cup, but fans will still be left wondering why more money wasn't ploughed into the team.

An astute loan signing was made in bringing Sunderland defender Liam Bridcutt to the Whites until the end of the season but permanent signings would have appeased the Leeds faithful more.

With top-scorer Chris Wood also currently out with a hamstring injury, the fans may also have hoped to see a striker come in as cover for the Kiwi forward, however again nothing came to fruition.

Even Steve Evans admitted that the club need better players if they are going to make themselves play-off contenders but the money simply was not spent by the side currently sat in 14th in the Championship, leaving many fans rightly dissatisfied with their club's business during the transfer window.

Do you agree with the teams that we think have had the worst transfer windows? Are they any other clubs that you would add to this list?

Let us know your thoughts on your club's transfer window by commenting below!