For an hour in the UEFA Super Cup final in Udine, Italy, Spurs were in dreamland. Two goals, either side of half-time, from defenders Micky van de Ven and Cristian Romero handed the North Londoners a shock 2-0 lead against reigning European champions Paris Saint-Germain. And truth be told, Thomas Frank’s men were good value for their lead.
As the game ticked into its latter stages, in-play odds providers couldn’t see a comeback transpiring. The in-play odds at Bovada listed the Parisians as long as 11/1 to lift the trophy at 2-0 down, and those odds drifted even further as the clock ticked past the 85th minute. But then, in true Spurs style, the Europa League holders capitulated late.
Tottenham’s Collapse
Lee Kang-in slammed home a brilliant left-footed strike in the 85th minute to reduce Parisian arrears. Then, deep into injury time, a well-worked move resulted in Goncalo Ramos nodding home from Ousmane Dembele’s picture-perfect cross to level up the scoreline and force a penalty shootout.
Even in the resulting spotkicks, Spurs still managed to gain – and surrender – the lead. Vitinha missed PSG’s first penalty, but van de Ven saw his spot kick saved by the Parisians’ new goalkeeper, Lucas Chevalier, before Mathys Tel slotted his penalty wide of the left-hand post. That gifted Nuno Mendes the opportunity to hand his side yet another piece of silverware in a trophy-laden 2025, and he duly obliged, comfortably beating Guglielmo Vicario to secure the win.
For Spurs, it was a familiar story. Play some brilliant football and deservedly take an unassailable-seeming lead, only to throw things away late on. New boss Thomas Frank will be hoping that his new charges can snap out of this never-ending narrative sooner rather than later. But unfortunately for the Dane, this story has been told countless times before. Here are Tottenham’s most ‘Spursy’ moments in recent years.
Battle of the Bridge
Stamford Bridge, spring 2016; the title race was still somewhat alive despite Leicester City’s huge lead at the summit. Tottenham raced into a shock 2-0 lead by halftime with Harry Kane and Son Heung-min on the scoresheet. Blue shirts rattled; the Foxes’ champagne remained on ice, but in the second stanza, the match turned feral. Duels got personal, tackles were supercharged, and Spurs’ stranglehold evaporated.
Gary Cahill cut the deficit with a scruffy finish on the hour mark. Then, seven minutes from time, Eden Hazard bent a gorgeous equalizer beyond Hugo Lloris into the top corner to make it 2-2 and hand Leicester the crown. The game produced a Premier League record at the time: nine Spurs players booked. That number tells the story. Tottenham didn’t just draw; they unraveled—psychologically and emotionally—and, in crunch moments, collapsed.
“‘Ze’ History of ‘Ze’ Tottenham”
The Champions League is merciless. Over two legs with Juventus, Spurs showed they belonged. A 2-2 comeback in Turin. Dominance at Wembley. Son Heung-min nudged them ahead before halftime in the second leg, making it 3-2 on aggregate and putting one foot into the quarterfinals. Then came the hinge.
Juve boss Max Allegri switched to a bog-standard 4-4-2 at half-time, and Spurs suddenly unraveled. Two breakaway goals in three minutes from strikers Gonzalo Higuain and Paulo Dybala put the Bianconeri ahead, and it was a deficit that Tottenham simply couldn’t claw back.
Tottenham had more of the ball, more shots, more control for long stretches. Juventus had the moments. That’s knockout football.
The post-match optics compounded the pain. Giorgio Chiellini’s line—“It is ‘ze’ history of ‘ze’ Tottenham”—wasn’t about talent; it was about habits under pressure. Switch off once, maybe twice, and the old campaigners will walk away with your season.
Fourth Place, No Champions League
Sometimes the cruelty is administrative. Under Harry Redknapp, Tottenham finished fourth in 2011-12. In most seasons, that’s good enough to secure qualification to the Champions League. But Chelsea won the competition that May with stunning victories, firstly against tournament favorites Barcelona in the semifinals and then against Bayern Munich, competing in their Allianz Arena home, in the final.
Their triumph saw them secure England’s fourth and final UCL berth, relegating Spurs to the Europa League despite their domestic exploits. No blown lead. No red mist. Just a rulebook twist that cut deep.
It felt like fate reaching across the table. A side built on Luka Modrić’s control and Gareth Bale’s surge—one of the most balanced Spurs outfits of the era—missed the elite stage through no fault of its own. To make matters worse, weeks prior, the Blues thumped Chelsea 5-1 in the FA Cup semifinal, adding insult to injury.
Already Relegated Portsmouth Rip Up the Script
On paper, a mismatch. Tottenham, stacked and surging. Portsmouth, relegated and reeling. On the grass, Wembley turned treacherous.
A poor pitch contributed to a costly slip from central defender Michael Dawson, allowing Portsmouth to seize their moment. Striker Frédéric Piquionne pounced to give Pompy a shock lead nine minutes into the additional period. Then, three minutes from the end, Kevin-Prince Boateng – once of Spurs – swept home from the penalty shot to hand the club in turmoil a stunning 2-0 victory and a second FA Cup Final appearance in three seasons.
Spurs created more, threatened more, and still tripped over the details that decide cup ties: precision in the box, clean footing in chaos, cool heads when frustration builds. That’s the essence of knockout jeopardy. Better teams can still lose if they let the game descend into a scrap. Portsmouth invited a scrap. Tottenham obliged, and they were punished for it.
