Tottenham Hotspur can inch closer to an elusive trophy with a Carabao Cup quarterfinal win: Are they ready?

Shortly before Manchester City embarked on their previously unthinkable run of one win in 11, they were the favorites heading into their EFL Cup round of 16 fixture at Tottenham Hotspur in October. This was not to discount Spurs – they were within touching distance of a top four spot in the Premier League thanks to a combination of talented players and an impactful manager. That said, it would take a lot to beat City, no matter who the opponent was.

Spurs found a way, though, advancing to the quarterfinals after a 2-1 win.

In addition to being the beginning of City’s slump, it was also a sign that Tottenham mean business. Manager Ange Postecolgou found a workaround for Pep Guardiola’s possession-oriented, attack-minded system that was generally unbeatable, repeating that gameplan a month later in a 4-0 win at City in league play. It was the type of statement victory that teased the potential of a deep run for Spurs and makes them one of the last heavy-hitters standing as quarterfinal action begins this week.

Spurs are now the closest they have been to a trophy since their run to the 2021-22 EFL Cup semifinals, their first trophy since 2008 within touching distance. As promising as Postecoglou’s Spurs can be at times, though, the way other parts of this season have unraveled forces a big question: Is it still too soon for them to actually end their trophy drought?

How to watch Tottenham Hotspur vs. Manchester United

• Date: Thursday, Dec. 19 | Time: 3 p.m. ET
• Location: Tottenham Hotspur Stadium — London, England
• Stream: Paramount+
• Odds: Tottenham Hotspur +130; Draw +295; Manchester United +180

A mounting injury crisis

Tottenham enter Thursday’s quarterfinal against Manchester United with just two wins in their last nine, their lone victories coming in that 4-0 win at City and Sunday’s 5-0 win at Southampton. While some of it can be attributed to Spurs’ own mismanagement of games, either by failing to live up to their attacking might or making defensive errors, much of it comes down to their long list of injuries.

Postegolou described the current injury crisis as the worst of his managerial career “by a fair stretch,” with Spurs down to just 18 available first team players. Those on the sidelines are pivotal players, too – goalkeeper Guglielmo Vicario fractured his ankle in that 4-0 win over City, while center backs Cristian Romero and Micky van de Ven returned from injury this month, only to pull up with injuries and return to the sidelines. Defensive option Ben Davies is also out for a few more weeks, while forward Richarlison has been prone to injury since joining Spurs in 2022. Midfielder Rodrigo Bentancur will also miss the game while he serves a seven-match ban for making discriminatory comments referencing teammate Heung-Min Son’s ethnic origin.

The lengthy list of unavailable players has thrown a wrench into Postecoglou’s plans of rotating through his roster to keep up with the demands of a jam-packed schedule, possibly leading a fatigued team into Thursday’s game. If Spurs are to win games during this injury crisis, though, Postecoglou made it clear that every fit will need to step up to the occasion or risk being excluded from participating. He yanked Timo Werner off at halftime of their 1-1 draw against Rangers in the UEFA Europa League last week, explaining why he had harsh words for the winger immediately after the game.

“I’m asking 18-year-olds to do some massive jobs and you want senior players – and he’s a senior player, he’s an international and he’s won the Champions League – there’s a level of application and performance you need to rise to to help the team. He didn’t reach that,” Postecoglou said in a Friday press conference, per The Guardian. “It wasn’t criticism, it was just an assessment of his performance and on a really challenging night for us, it needs to be better. We’re in a fight here, collectively we’re in a fight. I’m not going to go around worrying about people’s bruised egos. This football club, we want to achieve things and be successful. We’re down to the bare bones in players. If there’s somebody in the dressing room who’s fit, able to contribute, but who feels he needs something extra in this moment, he’s probably not the right type.”

A (very) long-term project

Postecoglou’s hire ahead of the 2023-24 season signaled a new project at Spurs, a fresh start after Jose Mourinho, Nuno Espirito Santo and Antonio Conte came and went in recent years without delivering and end to the silverware drought at the club. It felt like a successful reset, too, as new signings like van de Ven and James Maddison complemented the likes of Romero and Son to a fifth place finish, with Postecoglou successfully establishing an entertaining, attacking style of play. It was a solid foundation for Spurs to build upon in Postecoglou’s second season. After all, it was he Postecoglou himself who said he “always wins things in my second year,” per the BBC.

In several categories, Tottenham have grown from one season to the next. They are still one of the Premier League’s best attacking teams and averaging 2.3 goals per game this season, an impressive increase from last year’s 1.9, and have also improved defensively conceding an average of 1.2 goals per game after giving up 1.6 goals per game last season. They are only averaging 1.4 points per game in league play this campaign, though, down from 1.7 a year ago. Their inconsistency has been interpreted by some as a backward turn after making real strides last season, a failure for Spurs and Postecoglou to really click at a crucial point in the project.

While the injury crisis has made meaningful progress harder, the reality of this season’s Spurs team is that it is not terribly different from last year’s. While Postecoglou has been tasked with leading the team’s on-field advancement, Tottenham’s front office took a different approach over the summer. Minority owner and executive chairman Daniel Levy, the longtime frontman of Spurs’ growth, slowly evolved the club’s processes to resemble its top-flight counterparts, with chief football officer Scott Munn and technical director Johan Lange now leading the way. Last summer marked Lange’s first big transfer window with the club, during which five of Spurs’ six signings were teenagers. The lone exception was 27-year-old Dominic Solanke, who came off a 21 goal season for Bournemouth.

Lange’s approach signals that Spurs’ refresh is not going to be a quick one, even as supporters’ patience wears thin over the nearly 17 year trophy drought. That truth is particularly glaring when comparing Postecoglou’s second season to that of Mauricio Pochettino, whose shadow still looms somewhat large despite not winning a trophy during his five year stint in north London. Pochettino’s starters in the 2015-16 season, his second in charge, was impressive in several ways – Harry Kane was only beginning to make his case as one of the best goalscorers of his generation, while eventual World Cup winner Hugo Lloris and future Manchester City star Kyle Walker were also regular fixtures. The key to success for Pochettino’s Spurs, though, was that they found their player recruitment sweet spot quickly, signing players who were sneakily world class. The Argentine worked with the likes of Jan Vertonghen, Toby Alderweireld, Mousa Dembele, Christian Eriksen and Dele Alli in their peak years, while Son Heung-min was on the bench.

Postecoglou’s best lineup right now, even at full strength, looks more like a unfinished product than Pochettino’s group did in year two. World Cup champion Romero and center back partner van de Ven are the best recent signings of the bunch, while Dejan Kulusevski is making a case as Spurs’ player of the season so far. Even if the likes of Maddison, Solanke, Vicario and an aging Son can still put in a shift, though, Spurs still have too little cover in most positions and an argument can be made that there’s room for improvement in several positions on the pitch.

That is not to say that Tottenham will not eventually get there. The fact that they signed five teenagers in the summer suggests they have bet big on the future, and the minutes 18-year-olds Archie Gray and Lucas Bergvall have earned this season as a result of the injury crisis will likely go a long way in their development. It simply is not a squad traditionally built for winning now, even if Postecoglou is tasked with the delicate balancing act of dealing with expectations and realities.

A sense of opportunity

Tottenham have played in nine semifinals, three finals and booked one second place finish in the Premier League since they won their last trophy in 2008, losing different games in different ways. There are few underlying trends over the course of the last decade and change, minus one – Spurs are the sport’s textbook definition of a work in progress, and have been since Levy took over as chairman in 2001.

Then again, the work in question is pretty unprecedented. Levy has been charting an upward trajectory for a team that finished in 12th the season before he took charge, transforming Spurs into a team that has regularly competed for top four spots for more than a decade. He has done so in a new age for the sport, in which seemingly limitless wealth is the first qualification for a championship-winning team. No club who’s tried transforming into a juggernaut has pulled it off quite like Spurs, who have never boasted an owner with unusually deep pockets. It lends a lot of credence to the idea that the team are not simply doomed to fail in their pursuit of winning trophies, but that the reason they have fallen short is because it is just difficult – but not impossible – to do what they are attempting to do.

“I’m sick of that. That’s an excuse for me,” Postecoglou said on Friday when asked about the trophy drought, per Sky Sports. “I just think that’s an excuse. At the moment, I’m here. I take responsibility. These players, we’re here, so if we do think some mythical thing exists in this club that prevents success, we’ll change it. What’s the point otherwise? Don’t come here so I just don’t buy into that.”

The good news for Postecoglou and company is that cup competitions, in theory, place limited value on the obstacles in front of teams. Spurs bested City in the EFL Cup before their injury crisis kicked in, an example of the fact that there are still plenty of positives for the north Londoners. They are still one of the Premier League’s best attacking teams and clearly have the tools to beat City twice, but perhaps Spurs’ greatest advantage is that they have to play Manchester United.

United will arrive at Tottenham Hotspur Stadium a few days removed from their big win over City, but they are much more of a mess than Spurs are by many metrics. They rank 13th in the Premier League with only a +2 goal differential, the result of some poor scoring days, and boast a squad that will need more repair than new manager Ruben Amorim can offer as a midseason hire. Despite their recent struggles, Postecoglou has the advantage of already building a well-defined identity; Amorim’s newness will make that a challenge for United, and a 2-0 loss to Arsenal earlier this month suggests that it might still be too early for statement wins for the Red Devils.

This season has been a rocky one for Spurs, and though that might not change soon, Postecoglou’s side has an unexpected opportunity to prove their worth in a big way on Thursday. It is no sure thing that they will end this EFL Cup campaign with the trophy – after all, Liverpool and Arsenal are still in the competition and are the big favorites in their respective ties against Southampton and Crystal Palace. A first semifinal under Postecoglou’s leadership would go a long way of demonstrating progress from his first season to his second and inspire a new round of confidence in the project, however long they may be.