After the sacking of Antonio Conte and later his assistant, Christian Stellini, Spurs are once again looking to rebuild.
However, this time it is not just the squad that is needing a revamp. For a new head coach to be sold by the club's vision, they will need to appoint a sporting director first and foremost.
The era of Fabio Paratici was short and sporadically sweet, providing some quality signings in Cristian Romero and Rodrigo Bentancur, but simultaneously released Matt Doherty under very strange and preventable circumstances.
It is stability and direction that Daniel Levy will be looking for in his next appointment, with rumours suggesting three candidates are currently being considered.
Despite not being a leading candidate for the role, it wouldn't be the first time Spurs have acquired a Portuguese man who wasn't their primary target.
Having previously been at Benfica, Tiago Pinto is currently the Sporting Director at Roma and works alongside Jose Mourihno.
Given his recent success in Rome, alongside the free signing of Paulo Dybala, Pinto could be worth taking a punt on.
His ability to work with a low budget could prove an attractive proposition for Daniel Levy, who is unlikely to overspend on players given the expenditure of the previous summer transfer window.
Markus Krösche Eintracht Frankfurt's current Sporting CEO, Markus Krösche has recently been rumoured as the favourite to become the new Sporting Director at Tottenham and it is clear to see why.
The German has quite the CV, including back-to-back promotions with Paderborn, overseeing the Julian Nagelsmann era at RB Leipzig, as well as winning the Europa League with Frankfurt.
This appointment could reignite the club's pursuit of Nagelsmann, having previously worked with Krösche, a pairing that could cohesively create a winning culture at Spurs.
The signings of Christopher Nkunku, Dominik Szoboszlai and Randal Kolo Muani at his previous and current employers demonstrates consistently impressive recruitment, which increases Krösche's attractiveness to the North London club.
Daniel Levy and recently appointed Chief Football Officer Scott Munn will certainly look at a multitude of options, but the German will be high on the list.
With the recent news of Jordi Cruyff leaving his post as sporting director at Barcelona, he is now available for a new challenge.
The former Ecuador manager has been an integral part of operations at Barcelona, who comfortably won the La Liga title this season.
The last two years he spent in Catalonia, as both a Strategic Advisor and Sporting Director, will mean he has sufficient experience working at the highest level, something Levy may find attractive.
Cruyff also had no objections to Xavi working with youngsters and promoting youth players, something Tottenham should be advised to do with the current abundance of talent in their academy.
Once again, it is unclear whether Daniel Levy has selected a leading candidate for the role but Jordi Cruyff should certainly be considered given his recent achievement with Barcelona.
From major injuries to key players, to three different managers in the space of a month, it has been a season to forget for Tottenham.
Many fans will be hoping this campaign will end in European football, however, it may prove beneficial to have season to solely focus on domestic competitions, to end the clubs increasingly concerning trophy drought.