Opinion: The 10 best January transfer signings in Tottenham Hotspur history

Who are the best January transfer window signings in Tottenham Hotspur’s history? The North London club has done some great business in the mid-season window over the years, but we’ve compiled the best of the best.

The January transfer window is a perfect opportunity for clubs to regroup and reinforce their squads in the battle for titles and Premier League survival. It’s something Spurs have been pretty good at over the years, with many players coming in during the winter window and going on to do great things for the club.

Lucas Moura Dele Alli
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Who are Tottenham’s best January signings?

So, who is the best ever January transfer window signing for Spurs? Here are the top 10, including players who have scored crucial goals, achieved cult status, or are simply just a top drawer talent.

10. Louis Saha

OK, hear me out. Yes, Saha only played 12 games for Spurs in a six-month stint at the club, but he bagged four goals in that time (Transfermarkt), including one against Arsenal, which always helps your reputation among the Lilywhites’ faithful. Saha arrived on a free transfer, added some quality to the Spurs attack, and helped Harry Redknapp’s side qualify for the Champions League that year.

9. Jonathan Woodgate

Injury issues prevented Woodgate from ever truly fulfilling his potential at Spurs, with the former England international making just 65 appearances for the North London side over a three year stay at the club (Transfermarkt). However, he did score the winning goal in extra-time in the 2008 League Cup final, forever placing his name in Tottenham folklore.

8. Pedro Porro

We may only be a year into Pedro Porro‘s time at Tottenham but, despite a sticky start, the Spaniard has completely won the hearts of the Spurs supporters with his dynamic displays and creative output. The negotiations to sign the right-back lasted the entirety of January 2023, but he was worth all the effort and the money, and is now a key figure in Ange Postecoglou’s side.

7. Robbie Keane

With a whopping 122 goals in 306 games for Spurs (Transfermarkt), it’s impossible to overlook the contribution Robbie Keane made to the club during his two spells in North London. When he returned to Spurs in 2009 (technically in February, but as part of the January window), Keane continued his goalscoring feats, and remains just outside the top ten in the list of Tottenham’s all-time leading scorers.

6. Michael Dawson

After signing for Spurs in January 2005, Michael Dawson would stay at the club for close to a decade before moving on in 2014 to Hull City. When you talk about great servants to the Spurs cause, Dawson is a name you have to mention. With 321 appearances for the club, Dawson was part of the cup-winning side in 2008, as well as ushering a new era in the wake of Harry Redknapp’s departure.

5. Lucas Moura

Simply put, those three goals in Amsterdam in 2019 would have been enough to secure Lucas Moura’s legacy at Tottenham Hotspur for life, even if he never played another game. The miraculous turnaround in that Champions League semi-final against Ajax will never be forgotten, with Moura at the heart of one of the club’s biggest success stories in recent years.

4. Dele Alli

Things may not have gone to plan for Dele over the last couple of years, but there are very few young players who can boast the rise to stardom that this lad enjoyed in his early days at Spurs. Signed from MK Dons in the 2015 winter window, Dele would go on to register 67 goals and 61 assists for the Lilywhites across 269 appearances (Transfermarkt), and remains one of the most exciting talents to ever emerge in the Premier League.

3. Dejan Kulusevski

What an impact Kulusevski has had since joining the club from Juventus in January 2022. The young Swede had an electric start to his Spurs career, helping fire the club to the top four with his goals and assists in the second half of the 2022/23 campaign. He endured a difficult season under Antonio Conte last time around, but is right back in form now, and has even shown he can be effective in the 10 role as well as out wide. There is still so much to come from Kulusevski, which is very exciting indeed.

2. Rodrigo Bentancur

Another player who arrived from Juventus in that highly successful 2022 winter window, Rodrigo Bentancur is just pure class. It’s scary to think that we’ve barely even scratched the surface of what he is capable of, with injuries hampering his progress, but Bentancur has still shown he is capable of becoming one of, if not the best midfielder in the Premier League.

1. Jermain Defoe

Not content with being a brilliant January signing once, Jermain Defoe decided to leave Spurs for Portsmouth in 2008 and come back the following January to smash it at White Hart Lane all over again. A return of 140 goals and 31 assists in 361 appearances tells its own story (Transfermarkt), but Defoe truly was a magical little player for Spurs, and one of the club’s greatest ever goalscorers.

So, there you have it, the best ever signings for Spurs in the January transfer window. Here’s hoping Timo Werner and Radu Dragusin can make it onto this list in the future, as Ange Postecoglou’s Tottenham revolution continues to take shape.

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