Why Tottenham and trophies have never gone together – and why Ange Postecoglou must snap that streak

Tottenham’s trophy drought, for anyone who has not been paying attention, is ticking on towards 17 years.

More than 6,000 days have passed since Jonathan Woodgate’s header beat Chelsea at Wembley Stadium in the days when people still thought Carabao was a kind of reindeer.

But the great trophy-laden era for Spurs, 20-odd years of hauling serious silverware from the league and FA Cup Double of 1961 and a song about the glory of the cups at White Hart Lane, ended with the UEFA Cup win in 1984.

Four complete decades since have delivered one FA Cup and two League Cups. Fewer major trophies than Everton and Leicester City.

‘It’s in black and white,’ as Mauricio Pochettino would say when quizzed about winning something to show for five strong years, finishing as runners-up in the Premier League and the Champions League.

The idea that Tottenham and trophies should go together is something of a misnomer.

Desperation to compete with the elite drove them through Jose Mourinho and Antonio Conte

Ange Postecoglou has brought freedom and identity, but Spurs have had a rotten run of results

Yes, a big club with a huge fanbase, a fabulous stadium and a swish training ground, but while they were winning those three pots in 40 years, Manchester United won 31, Chelsea 21, Liverpool 19, Manchester City 18 and Arsenal 17. That’s without messing about with Community Shields, Super Cups, etc.

Spurs are lucky anyone still considers English football to have a Big Six not a Big Five.

Desperation to compete with the elite drove them through Jose Mourinho and Antonio Conte and a handbrake turn to Ange Postecoglou, fearing they lost something held dear along the way.

It cuts to the heart of the great Tottenham enigma. What matters most? Trophies or entertainment? They no longer feature Danny Blanchflower’s classic quote in the preamble to kick-off, but supporters of a certain vintage know it well.

‘The great fallacy is that the game is first and last about winning,’ said Blanchflower, captain of the Double winners in ‘61. ‘It’s nothing of the kind. The game is about glory. It is about doing things in style, with a flourish, about going out and beating the other lot, not waiting for them to die of boredom.’

While failing to win trophies in pragmatic style under Mourinho and Conte, everyone agreed there must be more enjoyable ways not to win anything.

Under Postecoglou they have reclaimed a sense of adventure and restored identity. At their best they exhilarate, although from their midwinter doldrums, sunk closer to the bottom three than the top four of the Premier League and in the grip of an injury crisis and a rotten sequence of results, reasons for cheer have been hard to find.

Protest songs aimed at Daniel Levy are back in fashion and if the chairman is under fire, then the manager is a little less secure, hostage to the promise that he always wins something in his second season.

Protest songs aimed at chairman Daniel Levy (centre) are now back in fashion in north London

Tottenham slipped to another defeat on Saturday with the team gripped by injury and illness

Postecoglou is now a hostage to his promise that he wins something in his second season

So, they could do with tangible success in one of the knockout competitions to relieve pressure and restore some faith in the plan as they go into this semi-final against Liverpool, the Premier League leaders, Carabao Cup holders and a team that scored six when they dropped into N17 last month. As my colleague Sami Mokbel reported last month, this semi-final is seen as crucial for Postecoglou’s future.

His ranks were depleted when Liverpool last visited and not much better off now.

There is £12.5million goalkeeper Antonin Kinsky, who is 21 from Slavia Prague and could go straight in after his work permit clearance came in on Tuesday. Rodrigo Bentancur returns from a ban. Radu Dragusin and Archie Gray, who played through illness against Newcastle on Saturday, feel stronger and 17-year-old flying winger Mikey Moore is back in contention after a virus.

With James Maddison and Pape Matar Sarr both suspended, however, there could be as many as 10 still missing.

These have been testing times for Postecoglou. His tense and irritable post-match manner does him no favours, but those who think he has not tried different things because his key message is he will not change his attacking policy are not looking closely.

His full backs have been reined in to accommodate the emergency in central defence and with Dragusin and Gray suffering from sickness against Newcastle on Saturday, he tweaked his usual 4-3-3 shape to provide more protection with two deep midfielders in a 4-2-3-1 formation.

It cost Maddison his place in the team and ultimately did not work as they lost again. That’s seven defeats in 14 games. Another bold call against Newcastle was to drop Son Heung-min, and it was probably with this tie against Liverpool in mind.

Son has not been at his best this season, playing more minutes than Postecoglou would have liked because of the absences of Richarlison, Wilson Odobert and Moore, and Timo Werner’s poor form.

New signing Antonin Kinsky could go straight into the team amid Tottenham’s injury crisis

Postecoglou has adapted in recent matches to protect a patched up Tottenham defence

Son looked flat in the 2-2 draw against Wolves in the final game of last year, missing a penalty before he was taken off after little more than an hour.

Postecoglou has given him a breather, a rare clear week with no fixture followed by half an hour from the bench against Newcastle in the hope he might be sparkle against Liverpool, because he knows he will need him.

Arne Slot, who Tottenham came so close to appointing instead of Postecoglou, has built the best side in the country and anyone searching for ways to trouble them will start by looking at the space behind their full backs, particularly behind Trent Alexander-Arnold if he plays.

Slot hinted at selecting a strong team at Spurs, defended Alexander-Arnold from criticism after Sunday’s draw against Manchester United and deflected it towards Ruben Amorim’s tactics.

‘We always try to find arguments,’ said Slot. ‘Nine out of 10 times the best argument is the quality of the team you face or their gameplan.

‘United had a very good gameplan: no build-up, just bring the ball long and not give us chance to press them high and go to a low block, which makes it difficult for any team to create chances, which we did quite a lot actually.’

Spurs need Son firing, and he will go into the semi-final feeling fresher and perhaps more settled after the clause was triggered to extend his contract until next year. ‘It’s great to extend his stay,’ said Postecoglou. ‘And the aim is to make sure he finishes his Tottenham career with silverware.”

Back to that. Trophies. A tall order, but Tottenham have beaten Manchester City and Manchester United to get this far so why not Liverpool? Why not dream of Wembley?

Son Heung-Min looks set to return against Liverpool and Spurs need him back at his best

Son could help exploit space behind Trent Alexander-Arnold should the Liverpool star feature

Tottenham have beaten Man City and Man United in the cup and will look to stun Liverpool

It would relieve the pressure building on the Postecoglou project.

Juande Ramos and George Graham, the last managers to trouble the Spurs trophy cabinet, might say it does not guarantee much more. Mourinho was fired less than a week before the Carabao Cup final, four years ago.

Ryan Mason was left to lead them through that defeat to Manchester City so the competition is not and can never be the ultimate target. Levy failed to mention winning it in 2008 when asked at a fans’ forum recently about his fondest memories from two decades in the chair.

He spent a billion on the stadium to host Champions League football but for Postecoglou stopping the clock on the trophyless years is an essential development.