After an impressive end to the summer transfer window, Tottenham Hotspur are expected to be back in the market again in January, with TEAMtalk ranking five options for the one position that currently stands out like a sore thumb – the left wing.
Spurs have made a strong start to the new season under new boss Thomas Frank, sitting third in the Premier League table and taking four points from their opening two Champions League outings.
Despite that, there have been a couple of teething problems for the Dane, one of which is how to get much more productivity out of the left side of the Tottenham front line.
Brennan Johnson and Wilson Odobert have so far tried and failed to claim the position as their own, while Xavi Simons is far better operating as the No.10 in the continued absence of James Maddison in particular.
With that in mind, TEAMtalk have ranked five attacking players who have all been heavily linked with a switch to Tottenham going back to the summer, in order of least likely to sign to most…
The Milan star was a player who was strongly linked with a move to north London in the closing days of the summer window.
However, it was Spurs themselves who backed away from a potential transfer, with the Italian giants reportedly demanding €100m (£87m) for the Portugal international.
After starting the new campaign with a calf injury, Leao has only recently returned to action and has scored once in three games so far.
He remains, though, a key man for the San Siro outfit and they are unlikely to budge from that sort of figure, especially for a player who remains under contract until 2028.
To that end, we have Leao as the least likely of the five players mentioned to move to Spurs in January.
DON’T MISS ➡️ Premier League signings of the season power ranking: New top two as Liverpool, Chelsea stars fall
The supremely gifted Monaco attacker was another player tipped to join Tottenham over the summer, only for the club to move on to other targets instead.
In truth, Akliouche is fourth on the list because he doesn’t really fill that left-sided void – although he could, at a push.
The 23-year-old has featured as a left-winger only three times in his career so far, with the vast majority of his games coming from the right. He can also operate inside, though.
Akliouche has scored twice and has one assist so far this season, having also started both of Monaco’s Champions League outings. Indeed, Tottenham will get a first-hand look at the classy attacker when they to France after the latest international break.
L’Equipe has previously reported that Monaco value the Ligue 1 outfit in the region €70m-€80m, although it’s thought he would be available for less than that.
Tottenham are reported to have jumped to the front of the queue when it comes to winning the race for the explosive Brazilian talent.
It’s claimed that Spurs scouts made a trip to South America last week to watch Vasco Da Gama winger Rayan, who has been setting the Brazilian top-flight alight this season.
The teenager is rumoured to have a release clause of €40m (£34.3m) in his contract, although it has emerged over recent days that Tottenham could face competition from the likes of Chelsea, Brighton and Nottingham Forest for Rayan’s signature.
And although reports from Brazil claim Spurs have already done groundwork on securing a work permit ahead of a new year move, the fact that Chelsea are in the mix is a massive worry – given their penchant for signing young Brazilian talent.
That’s part of the reason why we have Rayan at third on this list, with the fact that he is only 19 and unproven at Premier League level, also a concern.
To that end, Tottenham need a ready-made, high-level performer ready to step straight in, and while Rayan could be just that in the future, it’s important that Frank fixes that left-wing issue ASAP.
A player who had looked very likely to move to north London late in the summer window only for the switch to fall through.
Tottenham wanted to sign the former Everton man on a straight loan, rather than forking out the £43million it would’ve taken to get a deal over the line, meaning they ultimately missed out on his signature.
Lookman, who is capable of playing wide left or through the middle, had been out of favour at the start of the new season but has since returned to the Atalanta side.
The 27-year-old has scored a hugely impressive 52 goals and added 25 assists in just 121 games for the Serie A outfit, having rebuilt his career after struggling previously at Everton.
Lookman would give Frank a genuine goal threat from the left flank and also the option to play him centrally if needed. Add in the fact that he will be out of contract in the summer of 2027, and Tottenham should be able to do a deal in January for less than what they were quoted in the summer.
A real no-brainer of a move for a player who has had a tremendous start to the new season with Bournemouth.
Semenyo has already scored six goals and added three assists in just eight games for the Cherries this term, with half of those appearances coming on the left wing.
It’s no secret that Tottenham have held the player in high regard for some time, and TEAMtalk transfer insider Dean Jones has informed us that the club will properly assess the level of competition before committing to a bid for Semenyo in 2026.
The issue for Spurs, at this stage, is that Semenyo does not have a release clause and his price tag is only going one way – UP.
Indeed, TEAMtalk can also reveal that Bournemouth now consider the 25-year-old international teammate of Mohammed Kudus as a £100m player.
Now Tottenham has just received a £100m cash injection from majority owners ENIC to bolster their squad going forward, but the chances of them spending that on just one player are pretty slim.
Having said that, it at least shows some genuine ambition from the board and the realisation that big money is needed to get the club to where Thomas Frank wants them to be – challenging for ALL major honours.
Adding Semenyo on the opposite flank to Kudus would be a great start and also a nightmare match-up for opposing full-backs.
Let’s just see if they are now ready to take that plunge and smash their transfer record in the process.