There are not many to choose from very recently, are there? From the signings Mauricio Pochettino has helped make over the past five years, the majority have represented some very astute business by Tottenham Hotspur, whereas some others have struggled to adapt.
In more recent transfer windows, Davinson Sanchez, Lucas Moura, Serge Aurier, Fernando Llorente, Juan Foyth and Paulo Gazzaniga were all brought in the last campaign and they have all played their part in helping Spurs to develop as a football side and as a club.
Now we have briefly looked at some of the signings that have worked out rather well on the whole, here are two of the worst signings from the past five years…
N’Jie joined Spurs for a reported £12m fee in 2015 on a five-year deal.
For such a fee, it would have been fair to assume that in 14 appearances he would make more of an impact. Granted, his time at White Hart Lane was hindered by an injury but when the forward he did take to the pitch, he did little to impress at all, amounting no goals during his time in the capital.
The 25-year-old was then loaned out to Marseille the following season, that deal was then made permanent and it is there where he has continued his career.
Janssen looked to be the ideal back-up for Harry Kane upon his arrival in 2016; being a proven goalscorer; young enough to challenge Kane for numerous years which should him on top of his game.
Having just finished the season as the Eredivisie’s top-scorer, costing a reported £18.6m, Spurs fans had a right to be excited.
In his first campaign, he was rather clinical in both domestic Cups, yet he scored just two League goals and was loaned out to Fenerbahce for the season just gone, as Fernando Llorente was seemingly preferred as the second-choice striker.
The 24-year-old returned to Spurs this season and had been out of action until the New Year with a foot injury. He returned to play twice for the U23s in January, but he has since yet to be involved in a senior matchday squad at Spurs this season and looks set for an exit this summer.