It is a summer for big decisions at Tottenham Hotspur Stadium with the club having the perfect opportunity to reset after a frustrating few years in north London. Unable to build on their Champions League finish in May 2022, Tottenham will not be competing in Europe at all in 2023/24 after finishing the Premier League campaign in eighth.
Now with a new manager at the helm in Ange Postecoglou, Tottenham must also find a new managing director of football following Fabio Paratici's departure in April. On the pitch, Spurs have plenty to do in the transfer market with some fresh faces required to help take the team to the next level.
As important as it is that Tottenham get their business right in the transfer market with incomings and outgoings a must, one other area they must soon start to focus on over the coming weeks is the players who will soon enter the final two years of their contract. As a player's transfer value starts to decrease once they enter the last 24 months of their contract, this summer is the ideal time to either offer fresh terms or part with many in order to bring in a decent fee if they are not to be in the club's long-term plans.
The last thing Tottenham want to do is have a number of players go into the final year of their deal as that raises the very real possibility of them leaving for absolutely nothing once their contract expires. As things stand, Tottenham have nine players about to go into the last year of their contract, including main man Harry Kane.
So which players have two years left on their contract and what exactly could the future hold for them? football.london takes a look.
Alfie Whiteman
Transfer value: £400k (Transfermarkt)
Having spent time on loan in Sweden, Whiteman returned to the club in the winter and went on to sign a new contract with the club that runs until 2025. Fourth in the pecking order as things stand, the academy graduate, who turns 25 in October, is going to need to head off in order for regular first-team football at some point soon unless he springs a major surprise and breaks through at Tottenham.
READ MORE: The seven games Ange Postecoglou and Tottenham could be without Son Heung-min due to Asian Cup
As he isn't the most valuable of players due to his lack of first-team experience at Spurs, the Lilywhites could keep him as cover for this season before making a final decision over him next summer.
Verdict: Keep as cover
Japhet Tanganga
Transfer value: £6m
Tanganga really needs to move on this summer for the sake of his career after another injury-hit season. Injuries have stunted his development and he has only played 50 games for Tottenham in all competitions since making his senior bow in the 2019/20 campaign.
Given Spurs need to make some big changes in defence this summer, this is the ideal window for both parties to go their separate ways.
Verdict: Sell
Joe Rodon
Transfer value: £7m
Rodon is another who could also head off for a fresh challenge after limited first-team football over the past three years. The Wales international will be hoping a chance at Tottenham finally arrives under Postecoglou as he looks to make a name for himself at the club.
As he could well find himself down the pecking order once again, Rodon may be playing his football elsewhere on a permanent basis come August.
Verdict: Sell
Sergio Reguilon
Transfer value: £9m
Reguilon really needs to get a good season under his belt after an injury-hit loan spell at Atletico Madrid. The switch to a back four could work in his favour as he struggled when operating as a left wing-back and Postecoglou will no doubt take a look at him during pre-season training.
As Destiny Udogie appears to be the future for Spurs at left-back and with Ben Davies also on the books, Reguilon could be on the move.
Verdict: Sell
Ben Davies
Transfer value: £13m
Davies has served Tottenham incredibly well since joining from Swansea City in 2014. Excelling on the left of a back three under Antonio Conte, the Wales international was rewarded for his fine form with a new three-year deal last summer.
Capable of playing in a couple of positions and someone who always gives their all, he's a player Postecoglou and Tottenham need to keep at the club.
Verdict: Keep
Ryan Sessegnon
Transfer value: £15m
Signed in the summer of 2019, Tottenham are still waiting to see the very best of Sessegnon. Hit by a number of injuries in his time at the club, it really could be now or never for the player this summer as Postecoglou makes a decision over the squad.
Given that there's players ahead of him in the pecking order and his frustrating injury record, it perhaps is time to part with the 23-year-old so he can take on a new challenge.
Verdict: Sell
Pierre-Emile Hojbjerg
Transfer value: £39m
A regular in the Tottenham XI ever since joining from Southampton three years ago, Hojbjerg has been linked with a surprise exit from Tottenham Hotspur Stadium. It's not exactly clear if he fits into Postecoglou's system at present and he may find his chances limited come next season.
If Hojbjerg isn't to be part of the new manager's plans, Spurs should be able to bring in a decent fee for the Dane and use that money to strengthen elsewhere.
Verdict: Sell, if doesn't fit Postecoglou's system
Giovani Lo Celso
Transfer value: £12m
Having spent the past 18 months away from north London on loan, Lo Celso could be in line for a permanent exit this summer. Tottenham shouldn't be short on offers, with Barcelona and Aston Villa both linked with the Argentina international so far.
It seems the ideal time to sell the player and bring his Tottenham woes to an end in the process.
Verdict: Sell
Tanguy Ndombele
Transfer value: £19m
Signed in the same summer as Lo Celso, it has just not worked out at all for Ndombele either. Although Postecoglou's system appears to be made for him, it is his work off the ball that could prove to be his undoing if given a chance by the new manager.
Given his form over the past 18 months for Lyon and Napoli, clubs won't exactly be queuing up for his services on a permanent basis unless Tottenham are willing to part with him on the cheap. Ndombele is another that needs to exit Spurs in order to get his career back on track.
Verdict: Sell
Son Heung-min
Transfer value: £43m
Not enjoying the best of seasons and really struggling to find his top form, Son will be hoping for better luck in the 2023/24 campaign. Set to turn 31 next month, there is going to come a point where Tottenham need to plan for the future and bring in a long-term replacement for the South Korean.
He still has plenty to offer Tottenham, though, and they will more than likely want to keep him at the club beyond 2025.
Verdict: Keep
Troy Parrott
Transfer value: £3m
The 2023/24 season is a vital one for Parrott as he looks to achieve his long-term goal of becoming a Tottenham regular. Another campaign out on loan looks very likely, with the player really needing to hit the goal trail as he is ultimately going to be judged on goals as he is a striker.
Tottenham will then have a decision to make over the Republic of Ireland international next summer.
Verdict: Loan and then make final decision in 2024
Who would you keep or sell at Spurs this summer? Have your say below!