Ange Postecoglou could do with a last-minute miracle on January transfer deadline day - and it wouldn't be the first time. Not for Tottenham, at least, considering the club has pulled off some highly successful winter deals in the past. And it's exactly that kind of inspiration that wouldn't go astray for a club currently sat 14th in the Premier League. Spurs have already brought in goalkeeper Antonin Kinsky and Austria defender Kevin Danso (on loan from Lens) during this window. That's in addition to the signing of South Korea youngster Min-hyeok Yang, who will spend the rest of the season on loan at QPR.

Postecoglou is under huge pressure to turn Tottenham around in the second half of this season, and the right January business may be the key. With that in mind, Mirror Sport examines some of the club's finest winter work from previous January transfer windows. Not content with coming to Tottenham's rescue just once, club legend Jermain Defoe did so on two separate occasions. He first left West Ham for £7million in February 2004, then mimicked the move five years later when he exited Portsmouth for more than double that fee to eventually reunite with Harry Redknapp.

The end result was 143 goals in 363 appearances for Spurs, doing everything from helping the club survive relegation to getting them in the Champions League. It was towards the end of Defoe's first stint at the club that he lifted the 2008 League Cup, which remains their most recent major trophy. Another member of that iconic League Cup-winning side, Jonathan Woodgate was a late addition in January 2008. But he ended up proving himself worthy of Tottenham's £8m outlay after scoring in extra-time to down rivals Chelsea, earning Man of the Match honours for his troubles.

While his spell at Real Madrid ended up being far from what he dreamed, Spurs arguably got the best out of the eight-cap former England defender. Injuries eventually took their toll before Woodgate left London for Stoke in the summer of 2011, but Spurs got their value. Arguably the smartest January signing made under Mauricio Pochettino, Lucas Moura brought a verve to Tottenham's attack that few could mimic. The Brazilian was hounded by the likes of Manchester United in years gone by, but when the time came for him to leave PSG in the summer of 2018, Spurs moved quickest to snatch his services for £25m.

That wasn't the kind of money splurged easily in the winter at the time, but Lucas - who stayed until 2023 - gave Spurs a much-needed edge and helped squeeze the best out of Harry Kane for several seasons. He was part of the team that ventured to the 2019 Champions League final, and his 96th-minute decider against Ajax in the semi-finals became a thing of club myth. Spurs clinched the signing of Dele Alli for £5m from MK Dons in February 2015. The attacking midfielder spent seven seasons with the Lilywhites, scoring 67 goals in 269 games.

He played a big role in reaching the Champions League final in 2019 and the League Cup final two years later, as well as clinching a host of personal accolades (including back-to-back PFA Young Player of the Year awards). However, Alli suffered a rapid decline in his later years with Spurs, eventually leaving for Everton in 2021, and he has since gone on to play for Besiktas and Italian side Como. Michael Dawson joined Spurs on January deadline day in 2005 from Nottingham Forest, along with Andy Reid, for around £8m. He went on to become one of the Premier League's most formidable defenders during his time at White Hart Lane.

The centre-half reached two League Cup finals and won the first in 2008, eventually becoming club captain and being named Spurs' player of the year in 2010. He left the club for Hull City in 2014 having scored 10 goals in 324 appearances for Tottenham. Join our new WhatsApp community and receive your daily dose of Mirror Football content. We also treat our community members to special offers, promotions, and adverts from us and our partners. If you don't like our community, you can check out any time you like. If you're curious, you can read our Privacy Notice.