It is a huge week of football on the calendar for Ange Postecoglou and his Tottenham side. Victorious at Brentford on Sunday afternoon with a 2-0 win in west London, Spurs face two cup games over the coming days that could shape their season.
Travelling to Merseyside on Thursday evening to take on Liverpool in the second leg of their Carabao Cup semi-final, the Lilywhites are then at Aston Villa three days later in the FA Cup. Before those two games come around, Tottenham have the final day of the transfer window to try and negotiate.
A very frustrating month for the club with Antonin Kinsky their only arrival prior to the signing of Kevin Danso on Sunday, Tottenham will want to get another deal or two over the line as they look to boost their squad for the remainder of the season. There could possibly be another centre-back arrival following on from Danso, with Spurs also requiring another attacker after failing to entice Bayern Munich's Mathys Tel to Tottenham Hotspur Stadium.
Speaking on the signing of Danso prior to the Brentford game, Postecoglou said: “Brilliant (to get him). I think Kevin will be a great fit for us. We’re a little bit short at the back, have been for a while and he’s just really experienced, a good one-on-one defender.
"I’ve said before that getting new players in gives us energy and will give the group energy. I’m looking forward to him being part of the group.”
So what deals could Tottenham complete before Monday's 11pm deadline? football.london takes a look below.
Axel Disasi/alternative centre-back
Axel Disasi looks set to feature prominently in the headlines on deadline day with a Chelsea exit possibly set to come to fruition. The centre-back has found game time extremely hard to come by under Enzo Maresca and it may now result in him departing Stamford Bridge prior to the deadline.
Heavily linked with Aston Villa over the course of the month, Tottenham have come into the mix for the 26-year-old as they bid to add some cover to their depleted defence. What could scupper a potential move to Villa, though, is that Chelsea are competing with the Midlands club for a Champions League place and they won't want to directly strengthen a rival team.
That in turn may leave Disasi with a big decision to make in the final few hours of the winter market. If it isn't to be Disasi, Tottenham need to bring in an alternative centre-back following Radu Dragusin's injury and the question marks over Cristian Romero's return date.
Attacking option
Tottenham cannot afford to leave themselves too light in attack in the final few months of the season with so much still to play for. Dominic Solanke is still to return from injury and there is no guarantee Richarlison stays fit for the remainder of the campaign going on his injury frustrations at the club so far.
Tottenham are also light out wide at present, although they have Brennan Johnson, Timo Werner and Wilson Odobert to return in the not too distant future. A player who can operate on the wing and also through the middle would be the ideal winter addition for Postecoglou and the football club.
Johan Lange really needs to make it happen after their struggles in the transfer market so far this month.
Loan exits
Tottenham cannot afford to lose any of their senior squad before the deadline due to a lack of numbers but they could possibly sanction loans for their academy players. Will Lankshear departed the club on Friday evening after joining West Brom on loan for the remainder of the campaign, with the club making the decision to keep Dane Scarlett in N17.
Tyrese Hall is one player that would certainly benefit from a loan move as he needs to experience first-team football on a regular basis to help aid his development and the same goes for 22-year-old Max Robson. Damola Ajayi may have also come to the attention of some clubs following his Europa League exploits last Thursday.
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