Tottenham landed £23m Brazilian and former Real Madrid defender in January transfers

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Ange Postecoglou could certainly use a last-minute miracle as the January transfer deadline day looms - and it wouldn't be the first time for Tottenham.

The club has a history of pulling off successful winter deals, and that's exactly the kind of magic they need right now as they sit 14th in the Premier League. And Spurs have already welcomed goalkeeper Antonin Kinsky and Austrian defender Kevin Danso (who is on loan from Lens) during this window.

Postecoglou is under immense pressure to turn Tottenham's fortunes around in the second half of this season, and the right January business could be key. With that in mind, football.london takes a look back at some of the club's best winter work from previous January transfer windows.

Jermain Defoe

Club legend Jermain Defoe didn't just come to Tottenham's rescue once, but twice, in January windows. He first left West Ham for £7million in February 2004, then repeated the move five years later when he left Portsmouth for more than double that fee.

Defoe's contribution was significant, scoring 143 goals in 363 appearances for Spurs, helping the club avoid relegation and secure a spot in the Champions League. It was during Defoe's first stint at the club that he lifted the 2008 League Cup, which remains their most recent major trophy.

Jonathan Woodgate

A key player in that same League Cup-winning team, Jonathan Woodgate, joined Tottenham in January 2008. Despite being a late addition, he justified Spurs' £8m investment by heading home the extra-time winner against Chelsea at Wembley and bagging the Man of the Match award.

Although his stint at Real Madrid didn't live up to expectations, Tottenham arguably saw the best of the eight-time England international. Injuries eventually led to his departure for Stoke in 2011, but not before he had given Spurs their money's worth.

Lucas Moura

Lucas Moura is perhaps Mauricio Pochettino's most astute January signing. The Brazilian brought a unique flair to Tottenham's attack that was hard to replicate at the time (and perhaps still today).

Despite interest from Manchester United, Spurs were quickest to secure his services for £25m when Moura decided to leave PSG in 2018. This was a significant outlay for a winter transfer at the time, but Lucas - who stayed until 2023 - provided Spurs with a much-needed spark and helped bring out the best in Harry Kane for several seasons.

His last-minute goal against Ajax in the 2019 Champions League semi-finals has become part of club folklore. And while they may have fallen short in the final against Liverpool, fans will always have Lucas to thank for those injury-time heroics.

Dele Alli

Midfield magician Dele Alli was signed by Spurs from MK Dons for £5m in February 2015. The playmaker - now on the books at Como - spent seven seasons with the Lilywhites, netting 67 goals in 269 appearances.

He was instrumental in Spurs' journey to the Champions League final in 2019 and the League Cup final two years later, bagging a slew of individual honours - including consecutive PFA Young Player of the Year awards. However, Alli's form dipped dramatically in his latter years at Tottenham, leading to his move to Everton in 2021.

Michael Dawson

Michael Dawson arrived at Spurs on January deadline day in 2005 from Nottingham Forest, alongside Andy Reid, for a fee of around £8m. And he established himself as one of the Premier League's most reliable defenders during his stint at White Hart Lane.

The central defender reached two League Cup finals, winning the first in 2008, before taking over the captain's armband and being crowned Spurs' Player of the Year in 2010. He departed for Hull City in 2014 after netting 10 goals in 324 appearances for Tottenham.