Opinion: The familiar feeling of Cup defeat – Looking back at 30 years of Spurs pain

“Unless you have bad times, you can’t appreciate the good times”.

If that is the case, there will be an unfathomable amount of appreciation among Spurs supporters if, or hopefully when, they do eventually win another trophy.

Unfortunately, it will have to wait a little longer following last week’s Carabao Cup semi-final exit at the hands of Chelsea. It is becoming an all too familiar feeling for Spurs, but it wasn’t always this way.

I am of an age where one of my first footballing memories was Spurs’ 1991 FA Cup triumph. It was a cup run inspired by the individual brilliance of Paul Gascoigne, almost single-handedly carrying Spurs through the early rounds, setting up a semi-final with North London rivals Arsenal.

The stage was set and Gazza did not disappoint. In the 5^th minute of the game he scored one of the FA Cup’s most famous free kicks, accompanied by Barry Davies’ iconic commentary –

“Is Gascoigne going to have a crack? He is, you know. OH, I SAY. Brilliant. That…is…schoolboys’ own stuff.”

Spurs went on to win the game 3-1, setting up a final with Brian Clough’s Nottingham Forest.

Referring to the final in his autobiography, Gazza admits “I was a bit revved up, even before I got on the pitch.”

An understatement, to say the least. The final is best remembered for his two tackles that you could file under the ‘you wouldn’t get away with that nowadays’ heading.

The first, a studs-up, chest-high challenge on Garry Parker. The second, a reckless tackle on Gary Charles that, not only ended Gazza’s final prematurely through injury, but also resulted in a free-kick from which Stuart Pearce scored.

But even without their talisman, Spurs would turn it around. Goals from Paul Stewart and a Des Walker own goal in extra time secured an eighth FA Cup trophy.

On that afternoon at Wembley, few would have predicted the ensuing trophy drought – a 1999 Worthington Cup and 2008 Carling Cup aside – would last 31 years. And counting.

There have been highs, of course, but there have been significantly more lows. The lows are mainly categorised as a collection of ‘nearly’ moments.

Since 1991, Spurs have been to a further eight FA Cup semi-finals, losing on each occasion:

In each of these games, you could point to refereeing decisions, luck and injuries all playing their part. But a record eight losses is not just bad fortune.

The reality is that Spurs rarely have the innate ability that other top teams have – to get themselves over the line in big games.

After a last-16 Champions League defeat to Juventus in 2018, Giorgio Chiellini suggested Spurs lacked a mental toughness. “It’s the history of Tottenham,” he said, adding that Spurs “always miss something at the end”.

A harsh statement, but one that rings true. There is a mental fragility to Spurs at the business end of competitions. One that, almost certainly, is a double-edged sword. The history of near misses is bound to affect the psychology of the players and opposing teams will use that to their advantage.

It’s not just the FA Cup where Spurs have fallen short. Their League Cup exploits make for slightly better reading, but not by much. Since lifting the cup in 1999 they have reached the final on a further five occasions.

Four have ended in defeat and the other a 2-1 victory against Chelsea in 2008. In that same period, they have also lost three semi-finals, to Arsenal in 2007 and Chelsea in 2019 and 2022.

If ever a competition perfectly summarised the highs and lows of being a Spurs fan, it is the Champions League. There have been some memorable moments – Gareth Bale’s destruction of Maicon, that Peter Crouch goal at the San Siro, beating Real Madrid at Wembley.

But, by some considerable distance, the highest of highs was that night in Amsterdam. Having lost the first leg 1-0 at home, Spurs then found themselves 2-0 down at halftime at the Johan Cruyff Arena. An insurmountable deficit. Especially without their talisman, Harry Kane. Or so we thought.

Lucas Moura provided a glimmer of hope with a goal early in the second half. When he scored again four minutes later some more optimistic fans may have started to believe.

But the more realistic among us had been here before. When Jan Vertonghen headed against the bar late in the game any hope had vanished, surely? But the drama didn’t end there.

In the 96^th minute, Moussa Sissoko sends a hopeful ball long. Fernando Llorente wins the initial challenge with the ball falling to the feet of Dele Alli. His flick around the corner finds Moura, who hits it left-footed into the bottom corner.

Cue absolute bedlam. Celebrations on the pitch, delirium in the stands, Pochettino’s tears, an injured Kane running onto the pitch. An incredible night.

I would put myself in the category of a pessimistic fan – a lifetime of following Spurs will do that to you – but after the Ajax result, there were brief moments where I dared to believe. Very brief, I might add.

As expected, Spurs fans were brought crashing back down to earth in the final. Just two minutes in, the ball hits Sissoko’s arm and Liverpool are awarded a penalty. Mohammed Salah scores. It was the worst possible start and Spurs never recovered. A late Divock Origi goal putting the final nail into Spurs coffin.

It was a painful, but familiar, feeling as a Spurs fan. The semi-final had offered hope and promise. The final delivered the inevitable crushing disappointment. Two games that perfectly encapsulate the “history of Tottenham”.

However, let’s put this into perspective. Over this same period, there will have been fans of clubs who have never tasted silverware, or Champions League nights, or mixing it with the best teams in the Premier League.

But then you could argue that’s what makes it worse – to come so tantalisingly close to witnessing glory but ultimately falling short.

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