Spurs aren’t exactly renowned for their astute signings but this lot did quite well.
Tottenham Hotspur’s Jermain Defoe celebrates scoring
With January creeping around the corner, what better time to have a quick gander at Tottenham Hotspur’s most inspired winter purchases?
After all, no one does transfer windows quite like Tottenham Hotspur does transfer windows.
Dele Alli – from MK Dons, 2015
With never-ending price hikes and the rarity of English talent, it’s increasingly difficult to strike a bargain when negotiating the potential price of a player reared at home rather than imported on the cheap from abroad.

Yet, the initial £5 million (BBC) Spurs spent to secure the signature of an 18-year-old Dele Alli from League One MK Dons has proven a rather solid investment. After an inspired debut season, culminating in a richly deserved PFA Young Player of the Year gong, Alli’s price tag may well have multiplied tenfold.
Michael Dawson – from Nottingham Forest, 2005
Spurs fans never figured out exactly why Andy Reid was rated as one of the most exciting Irish players in his generation but, fortunately, his young team-mate lived up to his potential when he moved to the capital as part of the same deal.
While Reid’s nomadic career rarely lifted him above Championship level, Michael Dawson rewarded Spurs with nine years of consistency, reliability and, above all, leadership through periods of almost constant transition. One of the most underrated defenders of his era.
Jermain Defoe – from West Ham, 2004, and Portsmouth, 2009
He’s got his favourites has Harry. A year after bringing Defoe to Pompey in the winter of ’08, Redknapp switched allegiances to White Hart Lane and ensured that the England international, a prolific goalscorer during his 12 months at Fratton Park, was not far behind.

Defoe treated Spurs to 48 Premier League goals in his second spell, including a record equalling five in 90 minutes against Wigan Athletic but his deadline day swoop from London rivals West Ham five years earlier made it all possible.
One of England’s brightest young talents, The Hammers will forever rue letting their prized asset make the short switch north for just £7 million, per the BBC.
Robbie Keane – from Liverpool, 2009
Harry Redknapp knows how to spot a player, that much cannot be denied. It’s just a shame for Spurs that they seemed to flog all his favourites a few months before he arrived. Just half a season after a backfiring switch to Liverpool, the Republic of Ireland’s highest all time goalscorer returned to White Hart Lane in January 2009 for £6 million less than they sold him for, per the BBC.
Just don’t mention Del Boy.
Though a difficult second spell never quite lived up to his goal-laden first, Keane’s experience and technical quality helped guide Spurs up the table and lay the foundations for an ultimately successful Champions League push the following campaign.
Jonathan Woodgate – from Middlesbrough, 2008
While the coffers may argue otherwise, Woodgate’s proved rather priceless to Tottenham. After all, how can you place monetary value on memories, joy and the cold glint of silver? Injuries might have restricted the England international to just 65 appearances in four seasons at White Hart Lane but his towering header in the 2008 League Cup final remains Spurs’ only major honour this side of the century.

Alongside compatriot and centre-back partner Ledley King, Tottenham possessed two of the most gifted defenders in the country. It’s just a shame their bodies didn’t let them show it all that often.
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