Since the dismissal of Mauricio Pochettino in 2019, the north London side have embarked on a managerial carousel, first recruiting José Mourinho to deliver instant silverware through experience and pragmatism, only to be replaced by Nuno Espírito Santo after a short-lived experiment.

Antonio Conte then arrived with his demanding, win-now philosophy, before Ange Postecoglou ushered in a high-risk, high-intensity style that required yet another reset.

Speaking on these changes, Sherwood told Britain’s News Channel through OLBG: “It’s the consistency of their performances. I mean, they keep changing managers, keep the big turnover of players.

“I don’t think they’ve ever been shy on spending money. It just seems to be what they’re actually spending it on.

“And like I say, if you have a consistent performance, then you get results on the pitch and everyone’s happy. But it seems to be a very disgruntled fan base for a very long time now.”

While Tottenham have not been reluctant to spend, fans have criticised the recruitment, which they see as reflecting the manager’s preferences rather than a coherent, club-wide strategy.

|

GETTY

Players signed to thrive in one system have quickly found themselves ill-suited to the next.

The departures of established figures such as Harry Kane, Hugo Lloris and Jan Vertonghen removed not only quality but authority from the dressing room.

Their replacements have tended to arrive amid ongoing structural change, making it difficult for a settled hierarchy to emerge.

Comparing the current squad to the one Sherwood managed from December 2013 to May 2014, the former Spurs boss said: “Well, he’s certainly got more numbers than what I had.”

|

GETTY

He added: “But like I say, where’s the hierarchy? I had, what I felt was, was quite a special player in Mousa Dembele and I keep mentioning him, but I just felt like he gives me that control. Christian Eriksen, who was a player who would always play if he was fit.

“I had a player when I first went in there, who wasn’t even involved in the first team in Emmanuel Adebayor and I brought him into the squad.

“Now, Adebayor, in my opinion, on his day, was unplayable. And I had a very young Harry Kane coming through. He hadn’t played before. So, you know, gave him the opportunity to play and he repaid it and he went on to be the best player Tottenham have ever had in a Tottenham shirt.

“So, lacked quality, certainly in numbers and in depth, but I just felt like a little bit of better blend than what they have today. But I’m not sure that this group of players at the moment are being shown in the correct light. I think there’s a lot more to their game than what’s actually been on show.”

The scrutiny surrounding current manager Thomas Frank has intensified considerably, with BBC Sport understanding at least one member of the club’s executive team has actively proposed ending his tenure in recent weeks.

|

GETTY

Spurs currently sit 14th in the Premier League table, having managed victories in only seven of their 23 league matches this campaign.

Speaking on the lack of silverware the club has achieved in the Premier League era, Sherwood said: “You want to win trophies, and they won one trophy in God knows how many years, you know.

“And Ange Postecoglou was the man who was able to achieve that. So yeah, there has been big moments during that time and they’ve come up short.”

Until recently, a 17-year period without major silverware (from 2008 to 2025) was a primary source of criticism and mockery from rival fans.

While they have now won the 2024/25 Europa League, the perception of a long wait for success remains a part of their recent history.