Giovani Lo Celso, Gedson Fernandes, and Tanguy Ndombele - just a few of the many midfield signings made in the post-Mousa Dembele era at Tottenham Hotspur who have failed to deliver as expected.
Conor Gallagher, signed from Atletico Madrid on a £34m deal back in January, looks like the latest potentially flawed addition at N17, even after putting in arguably his brightest display to date against Brighton and Hove Albion.
The England international was a relentless, box-to-box presence in that dramatic 2-2 draw, albeit while still lacking that real quality in possession, with his 11 Premier League games at Spurs to date yielding just a solitary assist and just a solitary 'big chance' created.
His work ethic and all-action style is to his credit, but that little sprinkling of extra is still missing, with the 26-year-old in danger of heading the same way as those midfield reinforcements who have come before him.
Remembering Tottenham's worst midfield signings since 2019
That year also saw the aforementioned Dembele depart in the January, with Daniel Levy and co later signing Ndombele on a then-club record £62.8m deal in the summer, the first truly eye-watering sum dished out during Pochettino's tenure.
The Argentine was gone so soon into the former Lyon man's time in north London, however, with Ndombele never showing enough to warrant such a price tag, eventually departing in the summer of 2024 on a free transfer.
Fellow 2019, arrival, Lo Celso, also endured a difficult spell of his own after racking up just 18 goals and assists in 108 games for the club, while Gedson Fernandes' loan move ended after just 14 appearances for the Lilywhites.
Since then, there's been the mixed spell for Pierre-Emile Hojbjerg, as well as the recent loan capture of Joao Palhinha, the latter of whom appears unsuited to Roberto De Zerbi's new progressive approach.
That said, it is another member of De Zerbi's current ranks who can perhaps be considered the worst midfield signing since Ndombele.
Spurs need to finally sell the new Ndombele this summer
Eyebrows were raised at the selection of De Zerbi's midfield unit on Saturday, with Gallagher the only member of the trio to keep his place, as the young pairing of Archie Gray and Lucas Bergvall dropped to the bench.
The return of Rodrigo Bentancur, it must be said, was a welcome one, with the Uruguayan's recent absence coinciding with the club's slump in 2026.
The same can't be said of the returning Yves Bissouma, however, with it fair to say that the Malian's race is run in a Spurs shirt, ahead of his likely free transfer exit this summer.
Indeed, it would be a surprise to see the former Seagulls star offered a new deal at N17, with the £25m signing enduring a difficult few years at the club, both on and off the field.
This season, in particular, the 29-year-old has been a peripheral figure under a succession of managers, with Saturday's start having been only his ninth outing in all competitions.
Coincidence or not, Spurs are yet to win any game that Bissouma has played in so far in 2025/26, losing six of those nine league games this calendar year.
The latest of those appearances against his former club saw the once-promising midfielder hooked on 57 minutes by De Zerbi, having registered only 29 touches and picked up an early yellow card amid that difficult return to action.
In all, he failed to win a single duel or complete a single tackle, having made no key passes, no successful dribbles and only one progressive carry all game.
Hampered by injury and disciplinary issues throughout his time at the club, Bissouma - like Ndombele before him - has been a problem for a string of managers now at the Tottenham Hotspur Stadium.
A "ridiculous player at times" in the view of James Maddison - again, like Ndombele - that quality just hasn't been seen enough, ensuring he should be part of a real squad overhaul under De Zerbi this summer.
Regardless of whether or not Spurs beat the drop, the club hierarchy should be happy to let Bissouma walk away for nothing, just as they were for Ndombele two years ago.