Ranking Tottenham's last five January transfer windows from worst to best - Opinion
With the 25/26 winter transfer window now slammed shut, we have taken a moment to look back and rank Tottenham’s last five winter transfer windows.
The January transfer window for the 2025-26 season has since slammed shut, and Tottenham Hotspur, among several other sides, were actively involved in both securing new signings and sanctioning a few outgoings.
For Spurs, that business amounted to the signing of Conor Gallagher from Atletico Madrid for £35 million and the £15 million arrival of Souza from Brazil.
In terms of departures, Tottenham sanctioned several loan moves for fringe players and completed the £35 million sale of Brennan Johnson.
With the window now closed, it feels an appropriate moment to look back and rank the club’s last five winter transfer windows.
5. Tottenham winter transfer window 2025-26
Coming in fifth place, and firmly at the bottom of this list, is the ongoing 2025-26 season.
This window ranks among the worst in recent years due to Tottenham’s failure to meaningfully strengthen a severely depleted squad, with well over 10 players sidelined through injury and only one genuine first-team addition arriving in Conor Gallagher.
Souza profiles as a fringe option at best and will require a prolonged period of adaptation before being ready to start consistently.
That lack of impact is compounded by the fact that this was a window framed by promise, with reports of a £100 million cash injection.
In reality, Tottenham spent little more than £15 million net, with the £35 million sale of Brennan Johnson effectively funding Gallagher’s arrival.
A full-back and an additional winger were clearly required, yet Spurs emerged weaker rather than stronger after deadline day.
4. Tottenham’s January transfer window 2024
Spurs moved early in January 2024 to address two clear issues: a lack of pace and depth in attack, and the need for centre-back cover following injuries to Micky van de Ven and Cristian Romero.
Timo Werner arrived from RB Leipzig on loan with an option to buy, while Radu Dragusin joined permanently from Genoa for around £25.8 million, serving as extra centre-back depth.
Werner provided immediate width and pace during Heung-min Son’s absence, registering assists on debut against Manchester United and again versus Brentford, while Dragusin was viewed as a long-term investment despite limited early minutes.
Spurs eventually finished fifth, narrowly missing out on Champions League qualification, with the window seen as a step towards modernising the squad.
However, fast forward a few years into the future, and Werner could easily be labelled as one of the club’s worst pieces of business as he struggled during most of his time in north London.
As for Dragusin, the jury is still out on the centre-back who remains a backup option for both Romero and van de Ven.
3. Spurs winter transfer window January 2023
January 2023 saw Tottenham make two loan signings to address depth issues, particularly at right wing-back.
Pedro Porro arrived from Sporting CP on loan with a £39.5 million obligation, while Arnaut Danjuma joined from Villarreal on a temporary deal.
Porro endured a difficult debut in a heavy defeat to Leicester City but showed attacking quality over time, scoring three goals and providing three assists, eventually becoming a cornerstone under Ange Postecoglou.
Danjuma, despite scoring on his debut against Preston, struggled for minutes and finished with two goals across all competitions, often acting as an impact sub from the bench.
The window failed to arrest a wider collapse, with Rodrigo Bentancur suffering a season-ending ACL injury and Antonio Conte departing in March. Spurs finished eighth, missing out on European football entirely.
The 2024 window and the 2023 winter window are very similar, with little to separate them. Porro remains in the squad and still contributes, which places this window ahead of 2024.
2. Spurs winter transfer window January 2025
Second on the list is January 2025, a window defined by urgency, opportunism and contrasting domestic and European outcomes.
Spurs added Mathys Tel on loan from Bayern Munich, Kevin Danso from RC Lens on a loan with an obligation to buy, Antonin Kinsky from Slavia Prague for £12.5 million, and Yang Min-hyeok from Gangwon FC.
Danso provided much-needed depth in defence, making 15 appearances before his £21 million move was made permanent.
Tel contributed three goals across 20 appearances, while Kinsky impressed with his distribution during Guglielmo Vicario’s injury absence.
Despite finishing 17th in the Premier League, their lowest position in 48 years, Spurs’ winter reinforcements proved decisive in Europe, as they went on to win the UEFA Europa League.
That triumph ultimately secured Champions League qualification and marked the end of Ange Postecoglou’s tenure, with Thomas Frank appointed shortly after.
1. Tottenham January transfer window 2022
The January 2022 window remains one of the most influential in recent club history.
Dejan Kulusevski joined from Juventus on an 18-month loan with an option and obligation to buy, while Rodrigo Bentancur arrived permanently for £15.8 million plus add-ons.
Crucially, this season also saw Tottenham offload several high-profile players not in Antonio Conte’s plans, including Dele Alli, Tanguy Ndombele, Giovani Lo Celso and Bryan Gil.
Kulusevski immediately transformed the right flank, forming a devastating front three with Harry Kane and Heung-min Son, finishing the campaign with five goals and eight assists from 18 league appearances.
Bentancur brought composure and control to midfield, forming a reliable partnership with Pierre-Emile Hojbjerg.
Spurs surged post-January, overtaking Arsenal to finish fourth and secure Champions League qualification, underlining the impact of that window.
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