Tottenham's most gut-wrenching losses - and how they bounced back from them

You surprise me, Tottenham Hotspur.

Actually, no you don't. This is exactly what I expect of you. Therein lies the problem.

Wednesday's FA Cup elimination at the hands of a heavily-rotated second-tier Sheffield United means Spurs are likely to head into a 16th successive year without silverware.

Understandably, fans haven't taken it well. There's been a need for everyone associated with Spurs to go away and become a recluse in the middle of nowhere, to live in an abyss free of technology, to go on a retreat to another dimension, to detox to the point where every item of clothing in their wardrobe is beige and their favourite meal is a ham and cheese sandwich.

The Athletic's James Maw wrote a great/miserable/cathartic (delete as appropriate) piece on Tottenham's most humiliating cup exits of the modern era on Thursday, so do check that out.

This isn't the same concept. Spurs, like all sides, suffer at least one crippling defeat which makes fans question their love of the beautiful game a season, brings existential crises to the surface.

Ignoring the importance of the cups and shooting themselves in the foot on big stages now seems ingrained in the DNA of modern Tottenham, but do they immediately respond well to such blows? Are they able to salvage seasons? Would anyone like to hear me out, lift the mood a little?

If so, read on. It's going to be a bumpy ride.

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1. Bankrupt Portsmouth progress to FA Cup final (2009/10)

Context: Portsmouth, on the verge of going out of business and bottom of the Premier League by about 700 points, outlast a Spurs team filled with players they had to sell to them, winning 2-0 in one of the biggest semi-final shocks in the history of the FA Cup.

How Tottenham responded: Harry Redknapp's men beat Arsenal and Chelsea in their next two games (!!!), ultimately propelling them to a first appearance in the Champions League.

Verdict: The days where a first top-four finish was legitimately like a trophy. It all worked out.

2. Battered in the cup by...Fulham? Is this right? (2010/11)

Context: Now 20 years without an FA Cup, Spurs were ripped apart by Fulham in round four, losing 4-0 and conceding every goal in a manic first-half.

How Tottenham responded: A fortnight later, Tottenham beat Milan 1-0 at San Siro. Their extra rest for league games meant little though as they finished fifth.

Verdict: I don't think anything could ever justify a 4-0 loss at Fulham.

3. The first 5-2 (2011/12)

Context: After their faint hopes of a title charge were ousted, Tottenham were now fighting with Arsenal, Chelsea and Newcastle for a top-four spot. Their 5-2 hammering at the Emirates Stadium sent them into a tailspin.

How Tottenham responded: Between Redknapp's tax evasion trial, his unsuccessful flirtation with the England job and this battle-scar in particular, Spurs dropped to fourth after spending most of the season in third. Then their Champions League spot was robbed by Chelsea. Then Redknapp was sacked.

Verdict: This whole season needs the Men In Black mind erase treatment.

4. Basel on penalties (2012/13)

Context: Andre Villas-Boas' hell-bent pursuit of Europa League glory saw favourites Tottenham dumped out at the quarter-final stage by Basel on penalties. Mohamed Salah announced himself to the world, Emmanuel Adebayor skied a hilarious spot-kick.

How Tottenham responded: AVB's relentless desire to compete on the European front took its toll, with Spurs dropping a lot of points unnecessarily down the stretch and surrendering fourth place to Arsenal from an improbable position.

Verdict: Bad.

5. The entire 2013/14 season

Context: Gareth Bale left. Seven players came in. Most of them were rubbish. Tottenham got hit with a Tombstone Piledriver every other week. AVB lost his job. Tim Sherwood replaced him. Tim Sherwood simply existed. The end.

How Tottenham responded: A complete write-off season saw Tottenham actually make a smart move and hire Mauricio Pochettino.

Verdict: Worth it in the end, but god what a horrible timeline that was.

6. Chelsea win the League Cup (2014/15)

Context: Despite his disdain for cup competitions, Pochettino and Spurs stumble into the 2015 League Cup final. Jose Mourinho learnt his lessons from a 5-3 mauling at White Hart Lane a month earlier, starting Kurt Zouma in midfield and nullifying Tottenham, who lost 2-0 at Wembley.

How Tottenham responded: Spurs' intensity dropped for much of the rest of the season, but for a young team in the first year of a rebuild, that was understandable. Their foundations had been set.

Verdict: Inconsequential.

7. Chelsea kill the title charge (2015/16)

Context: Tottenham's push for the 2015/16 Premier League title was basically over by the time they went to Chelsea for what became known as 'The Battle of the Bridge' - it would have taken a miracle to overtake Leicester at that stage. After going 2-0 up, the Blues pegged them back to 2-2 to seal the Foxes' crown.

How Tottenham responded: Lost 2-1 at home to Southampton before succumbing to a 5-1 thrashing at 10-man relegated Newcastle.

Verdict: A meaningless collapse. No reason for it to happen, no real repercussions (apart from the 'third in a two-horse race' rhetoric).

8. Chelsea outlast onslaught to reach FA Cup final (2016/17)

Context: Blimey, quite a bit of misery induced by Chelsea here. Antonio Conte gets one over his future club when he brought on Eden Hazard, Diego Costa and Cesc Fabregas at 2-2 in an FA Cup semi-final, eventually winning 4-2.

How Tottenham responded: Spurs failed to catch Chelsea in the Premier League title race, but they would not have overtaken them even if they managed to win every remaining game. Instead, they ensured White Hart Lane's finale was memorable, beating Arsenal and Man Utd. Harry Kane smashed up Leicester and Hull to win a second successive Golden Boot.

Verdict: Annoying and frustrating, but Spurs did all they realistically could to make amends. It yielded a club record-high 86 points in the league.

9. The Juventus and Man Utd collapses (2017/18)

Context: Two cup exits in similar fashion. Tottenham led against both Juventus in the Champions League last 16 and Man Utd in the FA Cup semi-finals and looked set to learn from past mistakes. But they were a little fast-and-loose, naive when the pressure ramped up, losing 2-1 to both. The history of the Tottenham.

How Tottenham responded: Sandwiched between these defeats came Spurs' first win at Stamford Bridge in the Premier League era, seemingly overcoming a huge mental barrier. Yet they still threw away a meeting with Chelsea in the FA Cup final.

Verdict: Football can be confusing.

10. Champions League final (2018/19)

Context: Despite making no signings in the summer or winter windows, a tired and depleted Tottenham reached their first ever Champions League final against all the odds. The game is over after 24 seconds.

How Tottenham responded: Pochettino admitted pre-match he would have walked away if Spurs had won. In hindsight, that should have been the end of his first spell. The following season saw Spurs a little fresher physically but mentally spent, the final and end to that era still lingering. The Bayern 7-2, the Brighton 3-0 and Pochettino's sacking were late reactions to this night.

Verdict: Glorious failure. It couldn't be more Tottenham.

11. Norwich, the FA Cup and Eric Dier (2019/20)

Context: No Harry Kane, no Son Heung-min, no problem? Well, not quite. Mourinho's Spurs were knocked out of the FA Cup at the fifth round at home by relegation-battling Norwich on penalties because he had no plan without his two stars. Eric Dier climbed into the stands to confront fans aiming abuse at his family.

How Tottenham responded: This was the closest Spurs came to imploding. The COVID lockdown break meant they had time to recover Kane and Son for the rest of the season, preventing them from slipping into the bottom half. Even then, the club created controversy by placing non-playing staff on furlough.

Verdict: A pandemic saved Tottenham's blushes. Go figure.

12. Dinamo Zagreb's jailbird manager outwits Jose Mourinho (2020/21)

Context: Mourinho promised his Spurs players that they would win the 2020/21 Europa League if they qualified. They led Dinamo Zagreb, whose manager was in prison, 2-0 heading into the second leg of their last 16 tie. The Croatians rallied back and progressed to the quarter-finals.

How Tottenham responded: Mourinho lasted a few more weeks before being sacked, while captain Hugo Lloris gave an explosive TV interview urging the club to look at themselves. I'd go out on a limb to say this helped accelerate Daniel Levy's handing over of football operations, with Fabio Paratici arriving in the summer.

Verdict: Number one banter moment, there was no coming back from it.

13. Middlesbrough...yeah (2021/22)

Context: Tottenham's next win-now move saw them appoint ex-Chelsea boss Conte, who had reached the FA Cup final twice in his first two seasons in England. A strong Spurs team were eliminated by Championship outfit Middlesbrough in round five.

How Tottenham responded: Transitioning back to only playing once a week granted Conte the freedom to build a formidable team, leapfrogging Arsenal to fourth and reuniting a broken club.

Verdict: Probably worth it especially since Chelsea - who had already beaten Spurs four times without reply that season - were waiting for them in the next round.

14. Sheffield United, to be continued (2022/23)

Context: We know.

How Tottenham responded: Who knows?

Verdict: Jury's out but my scorching hot take is losing to a Championship team again is not going to age well.

Conclusions and takeaways

You're probably still wondering what the point of all this is, or if there even is one. Why did I open up old wounds and rub salt into them like a certain influencer standing over a steak?

It's impossible for Spurs fans to run away from the helpless feeling that the club's trophy drought may never end, like they're under some kind of medieval curse (I'm not categorically ruling this out).

But perhaps there is cause for optimism. Despite all the heavy blows over the last decade, Tottenham always land on their feet again relative to their goals and expectations, their resources and expenditure. As best pointed out by my good friend Tom Hayward on the Rule The Roost and The Tottenham Way podcasts this week, Spurs have never been driven to the brink like Chelsea this season or Arsenal and Man Utd in recent ones - even Sherwood ended his season with 69 points (though pre-pandemic Mourinho may have had something to say about this point).

Obviously, those more critical of ENIC's ownership and Levy's tenure will say more needs to be done with growing resources. That's fair. But even when Tottenham are unravelling, they find a way to pick themselves up and dust themselves off, even if it takes a year or so.

Spurs are still in a really good position to finish in the top four again and set themselves up for another summer of rebuilding and retooling. A bit of Groundhog Day and deja vu, but that's the best they can do right now. Either way, everything will be fine. Football is cyclical and always will be.