Tottenham 2023/24 pre-season - winners & losers

Tottenham Hotspur are entering the new Premier League season as one of the division's most intriguing sides.

They were expected to comfortably finish in the top four last season under Antonio Conte, but a series of implosions saw Spurs drop to eighth - their worst return since 2008/09.

Ange Postecoglou has been tasked with turning Tottenham back into a competitive and entertaining side, and the early signs this summer have been promising.

Though a friendly with Leicester City was called off due to poor weather and Roma were replaced as opponents by Singapore's Lion City Sailors, there have been plenty of positives to balance out the negatives of a disrupted pre-season.

Here are Spurs' winners and losers from the summer so far.

Winner - Ange Postecoglou

Straight off the bat, let's start with Postecoglou.

Since Mauricio Pochettino's sacking in 2019, Tottenham have seldom attempted to play front-foot football. There was a brief spell of free-scoring under Jose Mourinho during lockdown before he reverted to type, while Conte managed to secure fourth place in memorable fashion with Spurs morphing into a direct and formidable side.

But ultimately, the last four years have been largely miserable from an aesthetic point-of-view. There were question marks over whether Postecoglou could turn some of the squad's current cloggers into players capable of working well with the ball. The Greek-Australian has already shown anything is possible in that regard.

Postecoglou has also managed to win over doubtful fans with a series of impressive interviews and press conferences, again contrasting his doom-and-gloom predecessors.

The hard work truly starts for Postecoglou on Sunday away at Brentford.

Loser - Pierre-Emile Hojbjerg

"F***ing hell...play, play, play!" Postecoglou exclaimed on the touchline as Pierre-Emile Hojbjerg hoofed the ball into oblivion under no pressure during the first half of Tottenham's 5-1 win against Shakhtar Donetsk on Sunday.

90min were first to report in June that the new head coach didn't particularly fancy the Dane, and talks are currently ongoing with Atletico Madrid over a potential £30m deal.

Hojbjerg could yet stay and compete for his place, but he's not the type of graceful holding midfielder that suits Postecoglou's system. For the first time in his Spurs career, he has a real fight on his hands to break into the starting lineup.

Winner - Yves Bissouma

Yves Bissouma has looked a man reborn this summer, continually posting his jovial mood on social media following Postecoglou's appointment.

The former Brighton midfielder barely got a look-in under Conte, but seeing as he is the antithesis of Hojbjerg, he's been drafted into Spurs' starting XI throughout pre-season.

Injuries and niggles are the only thing standing in Bissouma's way from becoming a key starter heading into the new campaign.

Loser - Tottenham's Spanish full-backs

We've learnt nothing new about Pedro Porro and Sergio Reguilon this pre-season. Sure, they're great attacking options, but they still leave a lot to be desired going the other way.

The decision to sanction the £45m signing of Porro - a specialist wing-back bought for Conte, who was widely expected to depart soon anyway - in particular looks a glaring error from Tottenham.

Reguilon, meanwhile, will almost certainly not be a starter this season due to the emergence of Destiny Udogie.

Winner - James Maddison

Oh, how Tottenham have been crying out for a player like James Maddison for years.

Spurs failed to even provide competition for Christian Eriksen during his six-and-a-half season stay, let alone properly replace him upon leaving for Inter in 2020.

Maddison has built a strong on-pitch relationship with England teammate Harry Kane already and plays with the sort of ingenuity and fearlessness that Postecoglou craves.

Loser - Tanguy Ndombele & the 'Ndombelievers'

Every summer, Tottenham fans convince themselves into thinking this could be the year Tanguy Ndombele's talent outweighs all of his flaws. Every summer, they turn out to be wrong.

Injury has severely disrupted the Frenchman's pre-season, while in his absence, Pape Sarr, Oliver Skipp and even fellow outcast Giovani Lo Celso have shone.

90min understands Galatasaray are in talks with Tottenham over a potential transfer of Ndombele. His north London renaissance lasted roughly six weeks.

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