The last time Tottenham overturned a first leg deficit in the Champions League
Tottenham will have to overturn a first leg deficit on Wednesday night if they're to advance into the Champions League quarter-finals at Milan's expense.
Spurs have qualified for the last eight of Europe's premier club competition just twice in their history, so victory and progression will go a long way to lifting the mood in north London in what's been a mightily frustrating campaign.
Plagued by inconsistency, Antonio Conte's side have underwhelmed this term after promising so much with their summer business. New arrivals haven't quite settled, and their inability to sign a top centre-back to complement Cristian Romero has come back to bite them.
And despite suffering an inexcusable FA Cup exit at the hands of Sheffield United, Tottenham are still pretty well-placed to enjoy a decent campaign. Nevertheless, they have work to do if they're to continue on their European venture. Here's a reminder of the last time Spurs overturned a first leg deficit in the Champions League.
When was the last time Tottenham overturned a first leg deficit in the Champions League?
That night in Amsterdam. It's the greatest moment in Tottenham's modern history, but a contest that's now looked back upon with a hint of melancholy given everything that happened in the aftermath.
Talk about Spursy, eh? Fans can't even enjoy the most unthinkable of comebacks to progress into the Champions League final without dark clouds and the overbearing thought of 'what could've been' manifesting.
But this was a truly special night for everybody associated with Tottenham Hotspur; when Lucas Moura etched his name into Spurs folklore for eternity. It was the Brazilian who inspired Mauricio Pochettino's side over the line with a remarkable second-half hat-trick that absolutely nobody foreshadowed.
Erik ten Hag's babyfaced Ajax side were in dreamland. After stunning Europe's aristocracy to reach the last four, they took a 1-0 lead into their home second leg thanks to Donny van de Beek's early goal in north London.
The reverse fixture had all the makings of a procession. The Dutch side played with a verve and swagger that seemed to overwhelm the Premier League outfit, and they raced into a 2-0 half-time lead thanks to goals from Matthijs de Ligt and Hakim Ziyech. The Moroccan's strike was utterly superb, but Moura's heroics mean it's been lost in the abyss.
Cannabis sales must've soared during that 15-minute interval, with Ajax supporters inside the stadium meditating to Bob Marley's 'Don't You Worry 'bout a Thing' (they genuinely did). However, Lucas' rampage began just ten minutes into the second half before he equalised on the night following some dazzling footwork just before the hour. Game, from out of nowhere, on.
The nervous hosts held off Spurs' resurgence right until the last, spurning some golden opportunities of their own, before a hopeful punt upfield from Moussa Sissoko kickstarted a sequence that every Spurs fan on the planet can still recite today. Fernando Llorente's chest, Dele Alli's flick, "here's Lucas Moura...OH, HE'S DONE IT!!!!"
Jermaine Jenas couldn't believe it, Fletch. Nor could the entire football world.
Ajax 2-3 Tottenham (2018/19 Champions League semi-final second leg) - Starting XIs
Ajax: Onana; Mazraoui, De Ligt, Blind, Tagliafico; De Jong, Schone (Veltman 60'); Ziyech, Van de Beek (Magallan 90'), Tadic; Dolberg (Sinkgraven 67').
Tottenham: Lloris; Trippier (Lamela 81'), Alderweireld, Vertonghen, Rose (Davies 82'); Wanyama (Llorente 45'), Sissoko; Eriksen, Dele, Son; Lucas Moura.
What happened next?
The dreaded aftermath.
The 2019 Champions League final was pretty much over right after it begun. Spurs' big night was compromised by a pretty harsh handball call a minute into the contest as Liverpool's Mohamed Salah crashed home the opener from the penalty spot.
It was a drab affair in which Poch's side huffed and puffed without creating much of any substance. Semi-final hero Lucas Moura had a couple of half-chances off the bench, but that was about it. Divock Origi then thrust the dagger into Spurs' heart by adding a second late on as Liverpool lifted their sixth Champions League crown.
Pochettino's Tottenham died in Madrid that night, but it took a couple of months for the consequences to manifest. Despite an active summer, Poch was sacked in November 2019 after an indifferent start to the 2019/20 season, paving way for an alternate 'win now' approach which is yet to pay dividends.