We highlight five left-wing targets that Tottenham Hotspur could explore ahead of the January window, following their recent nine-figure cash injection.
Tottenham Hotspur received a huge boost ahead of the winter window following the Lewis family’s £100 million injection.
A portion of that amount is set to be made available for transfers, with Vinai Venkatesham and Johan Lange set to lead the recruitment strategy in January.
With that in mind, here are five left-wing targets Tottenham could realistically pursue in January to bolster their attacking depth and add more balance to the squad.
Kevin Schade is a familiar face for Thomas Frank
Thomas Frank has already confirmed that preparations for the January transfer window are underway, with Venkatesham and Lange leading discussions behind the scenes.
This winter, Tottenham could explore options to strengthen the flanks, particularly on the left side, where there is currently no guaranteed starter.
Wilson Odobert, Mathys Tel and Brennan Johnson have all featured there at different points this season, yet none have made the position their own.
Tottenham have been linked with Kevin Schade of Brentford, a player Spurs fans have described as a “baller”. Schade is a familiar face to Frank, having worked with him during his time at Brentford.
Since taking over at Tottenham, Frank has not yet reunited with any of his former players, with Bryan Mbeumo joining Manchester United and Yoane Wissa now at Newcastle United.
That could change this winter if Tottenham decide to make a move, although reports suggest a summer pursuit might be more likely. The German international has scored one goal in seven league appearances this season.
Tottenham could revisit deadline day star Ademola Lookman
Tottenham were keen to add more attacking depth right up until deadline day, and with a move for Savinho falling through, Ademola Lookman was seen as the reported alternative.
The Atalanta winger attracted interest from several clubs, not just Tottenham, but a deal never materialised as the Italian side were only open to a permanent sale rather than a loan.
Spurs could revisit a move for Lookman in January, although such a deal appears unlikely at this stage. Lookman would be a solid addition given his Premier League experience from his time at Fulham and Everton.
Tottenham have found success signing players familiar with English football, as seen with Joao Palhinha and Mohammed Kudus quickly adapting to Frank’s system.
Rafael Leao could be an expensive ace for Tottenham
It is rare for Tottenham to make a blockbuster signing in the winter window, which makes Rafael Leao a more ambitious option. However, Spurs are known admirers of the AC Milan winger, who has been linked with a move to north London in the past.
Leao has struggled for minutes this season due to a calf injury, but still managed to score in the Italian Cup after coming off the bench for just 17 minutes.
Tottenham would likely have to spend upwards of £70 million to sign Leao, with AC Milan valuing the Portuguese forward at around £100 million (€118 million).
While the move seems unlikely, Leao’s pace, flair and technical ability make him an ideal fit for the Premier League, and Tottenham’s growing financial power could see them test Milan’s resolve.
A surprise move for Jack Grealish next summer
Although this list focuses on January targets, Jack Grealish could be one for the summer. The England international, currently on loan at Everton, has rediscovered his form after a difficult spell at Manchester City last season.
Tottenham’s long-standing admiration for Grealish is well documented. The club were close to signing him in the past, and with his City future uncertain, the move could finally happen.
Everton took a chance on him in the summer after his falling out with City, and he has since earned the Premier League’s Player of the Month award for August.
Grealish is expected to be available for around £50 million next summer, and despite being 30, his recent resurgence could make him an appealing option for Frank. Joao Palhinha’s success at a similar age could serve as an encouraging example for such a deal.
Antoine Semenyo is Tottenham’s dream addition
Finally, Antoine Semenyo remains one of the most admired targets among Tottenham supporters. Many fans have even joked that the club should spend the entire £100 million cash injection on the Bournemouth forward.
Semenyo has made a flying start to the season, registering six goals and three assists in the Premier League.
Tottenham were in the race for Smenyo’s signature last summer, but the player chose to extend his contract at the Vitality Stadium for another five years.
The forward could have been available for around £70 million last summer, a figure that now looks like a bargain considering his current form.
Reports suggest Semenyo’s valuation could now reach £77 million (€90 million), but that would hardly deter fans who continue to urge the club to make a move for him.