Tottenham Hotspur were sitting pretty in third place when last season’s January transfer window reached a sorry conclusion. The club were keeping London rivals Arsenal and Chelsea at arms length, while the coattails of both Manchester outfits hovered tantalisingly close above them.

However, Harry Redknapp’s decision to purchase the dilapidated duo of Louis Saha and Ryan Nelsen arguably triggered a monumental collapse that would eventually mean they missed out on the bright lights of the Champions League. At present, Spurs are locked in a battle for fourth with rapidly improving Everton and surprise package West Brom, meaning the ability to learn from past mistakes has never been more important.

Andre Villas-Boas appears to have his feet firmly under the table at White Hart Lane, having finally brushed aside the smear campaign that seemed destined to execute his downfall. As a result, he must use this opportunity to stamp his own authority on an area of football where his predecessor was highly prolific.

A host of premium names have once again been linked with Tottenham, with fans inevitably dreaming of yet more inspired purchases. The spotlight will fall on Porto playmaker Joao Moutinho, who came within a whisker of joining the club in the summer. Other targets reportedly under consideration include Shakhtar Donetsk superstar Willian and Ajax starlet Christian Eriksen. Both players may strike you as mere figures of a proverbial pipedream, but how many people were caught aghast at Rafael van der Vaart’s arrival in 2010?

The January window is a notoriously difficult playground to conduct business in, especially as negotiations would typically last for weeks rather than days. Teams are increasingly reluctant to destabilise their squad midway through the season, which can lead to transfer valuations soaring through the nearest roof. I imagine both Liverpool and Chelsea are still paying for their rash moves for Fernando Torres and Andy Carroll, in more ways than one.

Nevertheless there are bargains to be had, glistening in the spring sunshine like diamonds in the rough. David Moyes and Alan Pardew benefited profusely from their courting of Nikica Jelavic and Papiss Cisse, which saw their respective seasons continue to flourish. It is this environment that brings out the best in chairman Daniel Levy as he hustles and haggles his way through numerous financially bewildering deals, but the budding relationship with his new manager will surely be put to the test as they both tussle to get their own way.

According to reports, the signing of Emmanuel Adebayor was the only purchase positively reinforced by Villas-Boas. Levy was the mastermind behind the acquisition of the likes of Gyfli Sigurdsson, Clint Dempsey and Hugo Lloris, which have perhaps hampered the Portuguese boss as much as they’ve helped him. It will be interesting to watch which targets - if any - the club are able to attract and whether we will witness yet another modern manager lament his lack of free reign in the transfer market.

Levy may have his intentions diverted elsewhere during the New Year, as the club look to finance their new £400m stadium. He will also be keen not to upset their creditable wage structure that has seen them triumph over adversaries Arsenal, even if they failed to do so on the pitch.

The startling statistic that reveals Spurs would be top of the table if games finished after 80 minutes is particularly interesting. Whether you consider such data fruitless or not, it could be evidence of an inferior mentality under Villas-Boas or a sign that the options on the bench simply aren’t good enough.

Either way, if the club wants to reaffirm their lust for Champions League qualification then they need to use this transfer window as a real statement of intent.

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