Is Spurs' FA Cup misery never-ending?
MIDDLESBROUGH, ENGLAND - MARCH 01: Tottenham Hotspur's Hugo Lloris during the Emirates FA Cup Fifth Round match between Middlesbrough and Tottenham Hotspur at Riverside Stadium on March 1, 2022 in Middlesbrough, England. (Photo by Alex Dodd - CameraSport via Getty Images)

Tottenham Hotspur's relationship with the FA Cup used to be prosperous. Now, their relationship couldn't be anymore shattered.

The defeat to Championship side Middlesbrough meant it has now been 31 years since the North London side won the oldest cup in the world.

My dad was 18 when he last saw Spurs win the trophy. This year, he turns 50. It perfectly captures the pain that the Lilywhites have had in the trophy ever since then.

He always talks about 'THAT' free kick against Arsenal from Paul Gascoigne and the joy he had seeing Spurs lift the trophy for a record 8th time at the beginning of the 90's.

However, at the beginning of 2022, trophies seem a distant dream for Antonio Conte's men. Many fans may be beginning to ask: 'when will the pain and suffering end?'.

  • Years of Disappointment for Spurs

Since 1991, Spurs have suffered their fair share of pain in the cup. The saying: 'it's the hope that kills you', couldn't relate anymore to the N17 side.

Every year, fans hope for glory, hope for success. Yet every year, they fall short of success, adding to the misery for fans.

The cup semi-finals against Chelsea and Manchester United in 2017 and 2018 hit close to home for fans. The squad Mauricio Pochettino assembled was the best they had for centuries.

It seemed a real possibility that trophies could come to the white side of North London. Jan Vertonghen and Toby Alderweireld at the back, Moussa Dembele in midfield and a young Dele Alli shining through. 

So for Spurs to lose both semi-finals against 2 teams they could beat on their day, showed that FA Cup success was so hard to come by in the 21st century.

But, it's not just these occasions where Spurs have fallen at the second to last hurdle. In 2012, they were embarrassed by Chelsea at Wembley, whilst defeat to Portsmouth at the same stage in 2010, topped everything else.

Since 1991, Spurs have lost an incredible 8 FA Cup semi-finals against some of their biggest rivals. The club seem to be unable to make the final step in the competition, with last night proving this even more.

  • Adding to the Misery

This years FA Cup felt like a real chance of success for Spurs. With United and Arsenal already out, Conte's men could have easily reached their first final since 1991 with a bit of luck.

Yet, last night's performance didn't surprise anyone. Any Spurs fan expects their team to let them down time and time again. It seems to be in the DNA of the club, something that Daniel Levy continually talks about.

It was a performance that lacked intensity, desire and passion from the players and staff, as a disinterested Conte looked on. Sluggish individual mistakes gifted the Northern side chances, whilst Tottenham's midfield failed to control the game.

This game was an opportunity to take a step forward. However, just like countless time this season, the Spurs side took another step back.

The result meant Spurs have failed to reach the quarter-finals since 2018. For a club that is classed as being part of the 'Big 6', this is a humiliating record for Daniel Levy and his ownership.

  • A bleak future ahead?

Once again, the defeat last night showed that Spurs' squad needs vast improvement. The Summer transfer window is vital for the club with 5 or 6 incomings drastically needed.

Yet, Spurs have had the squad to win trophies in the past. However, they've always fallen at the final hurdle.

Levy can invest fully in the squad, but there seems to be this psychological block for the North London side. The belief and confidence that they can win seems to be non-existent.

Pressure will be on Daniel Levy to keep his star names at the club in the Summer. Antonio Conte and Harry Kane have both hinted at leaving at the end of the season.

However, the hope for Spurs fans is that the Italian can give the club the belief it needs, so that it can take the final step to success.