Tottenham Hotspur's 15 Best January Transfers of the Premier League Era
With the January transfer window fast approaching, Tottenham Hotspur will be among the Premier League clubs deciding if they need to add to their squad.
Over the past two decades, they have used the month to recruit youth (such as Simon Davies and Anthony Gardner in 2000), as well as more experienced performers (Jonathan Woodgate in 2008, Jermain Defoe and Robbie Keane in 2009). Signings were made with the club battling relegation, as well as aspiring for English football's biggest prizes.
Just what—if anything—the club's transfer policy for this upcoming window will entail remains to be seen. Should technical director Franco Baldini and manager Andre Villas-Boas decide to dip into the market, they will be hoping to replicate the success of the best purchases by previous regimes.
Fifteen of those players are featured in the following list of Spurs' 15 best January* transfers of the Premier League era.
A few precede the implementation of the transfer window (back in 2002-03). Most come from the years that have followed, as the post-Christmas and New Year's comings and goings of players has become an annual event of some considerable hype.
*NOTE: In some later cases, such as Defoe's transfer to Tottenham in 2004, deals were completed in February. Essentially though, they were part of what is recognised as the January transfer window, hence their inclusion here.
15. Alan Hutton
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Along with Gilberto, Chris Gunter and Jonathan Woodgate, Alan Hutton was one of four new signings brought into the new Juande Ramos regime in January 2008.
Woodgate was known as a quality centre-back, but the most excitement surrounded the £9 million capture of the highly-rated, young right-back.
Hutton slotted straight into the Spurs team following his transfer from Rangers and was part of the team that beat Chelsea 2-1 in the League Cup final.
The Scotsman's momentum was slowed in 2008-09 by injuries. A season later, he went on loan to Sunderland in search of first-team football.
A brief resurgence at Spurs followed, sparked by a superb performance in a 3-1 win against the Wolverhampton Wanders that saw him score and win a penalty for Rafael van der Vaart.
His form did not stick, and with Kyle Walker having caught the eye on his loan spells at Queens Park Rangers and Aston Villa, Hutton was moved on.
14. Eidur Gudjohnsen
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It was a fairly minimal contribution, but Eidur Gudjohnsen played his part in Tottenham finishing fourth in 2009-10.
The former Chelsea forward moved back to London that January on loan after an unhappy spell with Monaco.
Gudjohnsen strengthened the Spurs' striking options as Robbie Keane moved to Celtic on a loan spell of his own.
The Iceland international started four times and made a further 10 appearances off the bench. His all-around play was decent enough, and he scored an important goal in a big 2-1 win away at Stoke City as Spurs established a strong run of form in the spring.
His other goal for Spurs came in a 3-1 FA Cup quarter-final replay win over Fulham.
13. Carlo Cudicini and 12. Radek Cerny
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Tottenham's two significant goalkeeping back-ups of the last decade (prior to the current situation at least), it is difficult to separate Radek Cerny and Carlo Cudicini. The only significant difference was in the circumstances of how each joined the club.
Cerny was originally brought in from Slavia Prague on an 18-month loan in January 2005, an arrangement that was extended a year later until 2008. Cudicini joined in January 2009 on a free transfer from Chelsea.
Among the uniting themes of their respective Spurs careers was a role in cup runs to Wembley.
Cerny was between the sticks for the team's League Cup semi-final victory over Arsenal. The Czech was unlucky to lose his place to Paul Robinson for the final.
Harry Redknapp used Cudicini as his goalkeeper for Spurs' FA Cup run in 2011-12. The Italian performed well until he and his teammates were exposed in a 5-1 thrashing by Chelsea in the semi-final.
When called upon, each goalie did his duty in the Premier League too.
Around the same time as beating Arsenal, Cerny was also being selected ahead of Robinson in the league and would finish the season as first choice.
Cudicini was called in at various points during 2010-11 in particular and would conclude the campaign deputising for Heurelho Gomes after the Brazilian suffered a succession of errors.
11. Ronny Rosenthal
4 of 13Bought in January 1994 for £250,000 from Liverpool, along with Kevin Scott, Ronny Rosenthal was one of two winter signings made by Ossie Ardiles as he looked to ward off the threat of relegation.
Rosenthal would go on to feature 100 times for Tottenham. Ardiles' successor Gerry Francis predominantly used the attacker in left midfield, and he was a fixture in the side, particularly during the 1995-96 campaign.
"Rocket" Ronny will best be remembered, though, for a stunning display against Southampton in a fifth-round FA Cup replay in March 1995.
Having gone two goals down at The Dell, Rosenthal came on to instigate a second half fightback of epic proportions (see video above).
The Israel international scored twice to take the game to extra-time. There he scored a second, stunning, long-range effort to complete his hat-trick and set Spurs on their way to a 6-2 win.
10. Andy Sinton
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In an era when David Ginola was marauding the flanks of White Hart Lane and beyond, it is easy to forget the less glamorous Andy Sinton.
Though not in possession of the Frenchman's level of flair, the occasional England international was skillful in his own right. His ability, coupled with an excellent work-rate, allowed him to thrive on the wing or occupy a creative role centrally.
Signed by Gerry Francis in January 1996 from Sheffield Wednesday, Sinton really came to the fore the following season. In an injury-hit campaign for the club, the recently turned 30-year-old was good for 36 appearances, with goals coming in wins over Sunderland, Coventry City, Blackburn Rovers and Middlesbrough.
Sinton's reliability was missed in the latter half of 1997-98, as injury cost him his part in Spurs' fight against relegation.
Back to full fitness the year after, he was again a model of consistency. Featuring in the latter rounds of the competition, Sinton earned a winner's medal for his part in Spurs' League Cup success of 1999.
9. Mido
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Unfit following minimal playing time during his half-season spell with Roma, Mido's main impact at Tottenham would come in the latter two-thirds of his 18 months on loan there.
The striker's 11 goals in 2005-06 helped the improving North Londoners to within reach of qualifying for the Champions League. The quality of the Egyptian's performances tailed off after a contentious time at the African Cup of Nations that season, but overall he did well in serving as the more physical foil to either Jermain Defoe or Robbie Keane.
It became apparent shortly after his initial arrival in January 2005 that Mido had considerable talent to contribute when on song.
His debut against Portsmouth ranks among the best seen in a Spurs shirt in recent times. In a 3-1 win he scored twice and won over the crowd with a showcase of skill that verged on the sublime.
Mido would score once more in 2004-05 in the FA Cup, but that season was largely a write-off as he got himself fit.
He joined Spurs on a permanent basis for the 2006-07 season, but life as Dimitar Berbatov's back-up did not appeal in the long run.
8. Robbie Keane
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Robbie Keane's second spell at Tottenham would not replicate the success of his first one between 2002 and 2008. Nonetheless, his return in early 2009 following a brief stint with Liverpool did achieve its primary function of helping Spurs to avoid relegation.
Harry Redknapp brought him, Pascal Chimbonda and Jermain Defoe back to the club, as well as recruiting Wilson Palacios to the cause.
Keane was typically lively and energetic up front, setting the tone for his team in a way they duly followed.
He scored five times during the remainder of that season, including in a win over Middlesbrough and a draw with Sunderland that helped to turn the momentum in Spurs' favour.
7. Simon Davies and 6. Anthony Gardner
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With all due respect to Matthew Etherington (£500,000 from Peterborough United)—the third of a trio of acquisitions from the Football League in January 2000—it was Simon Davies (£700,000, also from Peterborough) and Anthony Gardner (£1 million from Port Vale) who proved to be the most value for the money for Tottenham.
Signed with long-term intentions, they were soon enough adding a youthful vitality to a team whose main parts were pushing or already over 30.
Both players' Spurs careers ultimately did not turn into lengthy stays. While they were in North London, though, they were solid contributors during a time when the club was transitioning from mediocrity to a more competitive proposition.
On the wing, Davies quickly established himself as a talent to watch.
Spurs members voted him their player of the year in 2002 (prior to it being awarded at the end of each season). At his best, he was quick and inventive, a player to light up the duller days.
Inconsistency would ultimately be his downfall at Spurs. While well aware of what he was capable of, by 2005 the club were moving in a direction where more would be required.
Gardner was undone by injuries, but for the best part of eight years he was a useful defensive presence.
The early years were his most consistent, as he proved himself a more than capable Premier League centre-back.
As was the way with a Spurs team that too often flattered to deceive, Gardner too would have his off days. When concentrating and fully alert to that which was going on around him, though, the physically intimidating defender could be dominant.
Such displays earned him an England call-up in November 2003, a season that was to be the only one he played in more than 30 times. Thereafter, he would only intermittently be allowed to shine.
5. Wilson Palacios
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Of those players brought in by Harry Redknapp in the 2009 January transfer window, none had a more important immediate impact than Wilson Palacios.
Tottenham were still battling to overcome the handicap they had given themselves following their awful start of two points in eight games that season.
The situation had initially improved after Redknapp had replaced Juande Ramos. Form soon turned against Spurs though, and from December to mid-January, they only won one league game in seven.
"He will come in here and get after it and play aggressively," Redknapp told BBC Sport after Spurs paid Wigan Athletic £12 million for Palacios. "He will work and close and run. I feel that we need a bit of that around the place."
The Honduran obliged, giving Spurs some much-needed steel in midfield to balance the energy and skill of players like Jermaine Jenas and Luka Modric.
With a tougher core, Spurs got it together and eventually finished eighth. Without Palacios, 2008-09 might have been a lot harder going than it was.
While remaining a regular contributor the following season, Palacios' form fell away as his team's performances improved to the extent his talents were not so regularly required.
In February 2011, in what turned out to be his third last game for the club, he produced arguably his finest display.
Sitting alongside Sandro in central midfield, the quiet but determined Palacios was excellent as Spurs stood firm to record a famous 1-0 win over AC Milan at the San Siro.
4. Younes Kaboul
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Brought back to Tottenham in January 2010 by the man who had signed him for Portsmouth one season earlier, Younes Kaboul was as shrewd an acquisition as Harry Redknapp made.
Originally joining Spurs in 2007, the talented but very green Kaboul moved to the South Coast a year later in search of a more understanding environment and regular first-team football. He developed considerably at Fratton Park, and Spurs reaped the benefits when he returned.
Spurs' push for Champions League qualification in 2009-10 saw the Frenchman feature at right-back. His improved defensive qualities and powerful running style made him an able deputy, but his talents clearly lay in central defense.
Kaboul was deployed there with increasing regularity, though it was a goal in Spurs' 3-2 North London derby win that would be the main highlight of his first full year back in North London.
In 2011-12, everything seemed to come together for Kaboul. Making a career-high 39 starts, he was a rock at the back as Spurs' superb form in September through February even led to talk of a title tilt.
That fell away, as did Kaboul's own performances slightly after missing a couple of games through injury. Still, after a largely impressive year, he was expected to push on from there.
Fate intervened, with injuries robbing him almost all of the 2012-13 campaign. Having now recovered and looking like finding match fitness, we wait to see what is next for Kaboul in his Spurs career.
3. Jonathan Woodgate
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As has been the theme through much of Jonathan Woodgate's career, injuries ultimately conspired to stop his time at Tottenham being as good as hoped.
It was far from a bust. He featured 64 times, playing regularly in his first year-and-a-half, albeit during a period when Spurs were struggling for consistency in the league.
Woodgate earns the lofty place on this list for one performance in particular. Or to be more precise, one moment.
Having only just moved to Spurs following a career-rejuvenating spell with Middlesbrough, Woodgate found himself starting against Chelsea in the League Cup final in place of the injured Michael Dawson.
Alongside Ledley King at the back, Woodgate performed valiantly as his team fought back from a goal down to take the game to extra-time.
Four minutes in, the centre-back got the better of an aerial contest with Petr Cech, heading the ball past the Blues' keeper into the empty net.
Spurs held onto their 2-1 lead. Woodgate's goal won the club what remains their only silverware of the 21st century so far.
2. Michael Dawson
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Essentially the "lesser" part of the £8 million deal that brought him and his Nottingham Forest teammate Andy Reid to White Hart Lane in 2005, Michael Dawson has gone on to more than prove his worth.
Dawson's transfer was not greeted with the amount of publicity that came with Reid's. But after starting five games that season, the defender would soon begin fulfilling his top-flight potential in a way the Irishman was unable to.
Seeing off the competition of fellow centre-backs Noureddine Naybet and Anthony Gardner, Dawson went about establishing a partnership with Ledley King.
Over the next few years, both would suffer from injuries that would stop them playing together as often as they would like. When they did combine, they were as effective a defensive duo as Spurs had seen in several years.
After playing a big part in his team's Champions League qualification in 2009-10 (as well as in the heroic displays in the competition versus AC Milian in 2011), Dawson endured a stuttering few years as injury and the form of others limited his game time.
Having convinced his current boss Andre Villas-Boas of his ability, he is enjoying as long a run as he has ever had in the team. With competition in defence fiercer than it has ever been, though, the Spurs skipper knows he cannot rest on his laurels for a second.
1. Jermain Defoe
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Jermain Defoe could feasibly be on this list twice. He initially joined Tottenham in the 2004 January transfer window and, after a year with Portsmouth, rejoined the North Londoners in the same month in 2009.
Both halves of his Spurs career have had their ups and downs. Yet with the striker having now reached fifth in their all-time top scorers list, his signing(s) definitely ranks as some of the best business done by the club in any month.
On both occasions Defoe was brought in to help stave off the threat of relegation.
After David Pleat gave West Ham United £7 million and Bobby Zamora for the then-21-year-old's services during the 2003-04 campaign, he did just that, scoring seven times as Spurs finished 14th. Injury denied him the chance to make as substantial a contribution five years later, but his return played its part in lifting Spurs out of a mid-winter funk and into safety.
Important as these initial improvements to the team were, it is Defoe's overall time with Tottenham that earns him the No. 1 spot on this list.
With 142 goals, he has been one of Spurs' significant players of the era. His two best seasons (2004-05 and 2009-10) saw him play a leading role in helping the team return to a relative prominence in the English game—notably marked by Champions League qualification in the latter campaign.
Defoe is finding playing time hard to come by in the Premier League right now. Regardless of what his Tottenham future holds, the forward has more than made his mark for the club that has been his home for the majority of his career.
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