For Tottenham fans, the Champions League was once viewed as a special VIP club. And for many years, Spurs were met with aggressive bouncers at the door.
Under Mauricio Pochettino, that all changed. Tottenham went from the easy pick for sixth place into a top-four lock. completely elevating the standards at the club.
Those changes culminated in arguably the greatest cup run that didn’t end with lifting a trophy at the end of it. How very Spurs.
Here’s the definitive timeline of Tottenham’s remarkable run to the 2019 Champions League final…
For the second season running, Spurs were drawn into the Champions League’s ‘group of death’, this time alongside Barcelona, Inter and PSV.
First up was a trip to San Siro as Pochettino’s men looked to bounce back from two successive defeats in the Premier League.
Inter, returning to the European Cup after a six year absence, were completely outplayed for 85 or so minutes, with Christian Eriksen’s deflected effort setting Spurs on their way to victory.
But Tottenham wilted under late pressure – pretty much the only defending they had to do all game – and Mauro Icardi and Matias Vecino completely turned the game on its head.
When Tottenham beat Real Madrid in 2017, it didn’t really feel like that much of an upset. Sure, Zinedine Zidane’s side had won back-to-back Champions Leagues and would eventually three-peat, but Spurs were emerging as one of Europe’s best outfits.
But the narrative had flipped a year later when Barcelona came to town. Tottenham were missing several key players – both Eriksen and Dele Alli, who had scored Spurs’ goals in the Madrid win, were injured. The Wembley pitch looked like Wandsworth Common after a bank holiday weekend.
The 2-4 scoreline was a respectable one considering how incredible Lionel Messi was on the night without even needing to get out of first gear.
A 2-2 draw at PSV should have been when Spurs’ Champions League campaign died. Hell, everyone thought it had at the time.
Hugo Lloris was given his marching late in the second half with Spurs 2-1 up, and Luuk de Jong equalised to ensure Tottenham had just one point after three group games.
Pochettino went bold for the reverse fixture at Wembley, starting Harry Winks at the base of a 4-3-3 that also included Alli, Eriksen, Lucas Moura, Son Heung-min and Harry Kane.
So obviously PSV went ahead in the second minute.
But Tottenham remained resolute and were rewarded for their persistent attacking efforts. The Dutch side couldn’t deal with substitute Fernando Llorente, who played a huge role in both of Kane’s late goals to keep their hopes of qualification alive.
Tottenham knew a win at home to Inter would see them leapfrog the Italians and head to Camp Nou on the final matchday with their fate in their own hards.
A tense affair at Wembley was settled by Eriksen following some remarkably selfless play from Moussa Sissoko and Alli.
Spurs knew that they only needed to match Inter’s result in their respective final group games in order to reach the last 16, and it was a night which swung wildly in both directions.
Tottenham fell behind to Barcelona early on after Ousmane Dembele sliced them open on the counter attack, but they were handed a reprieve when PSV took the lead at San Siro.
While Spurs were on top for much of the night at Camp Nou, they were yet to find a way through. Inter, however, found an equaliser in the last 20 minutes and were pushing on for the win.
Lucas Moura at last pulled Spurs level in the dying embers but would only be able to secure a point as players and fans waited for news to filter through from Italy.
Inter had an incredible chance to knock Spurs out with virtually the last kick of the ball in the group stage, only for Nick Viergever to tackle Mauro Icardi just in time.
Tottenham had advanced to the knockout stages by the skin of their teeth, but totally deserved over the course of six games, particularly when factoring in their rubbish start.
For the third time in four seasons, Spurs were drawn with Borussia Dortmund in Europe.
Lucien Favre’s side had emerged as a real contender after giving Bayern Munich a test in the Bundesliga title race, and Tottenham would have to play at least one leg without Kane and Alli.
But Son – nicknamed ‘the Bee Keeper’ in Germany because of his prolific record against Dortmund – was relishing the role of the main man.
He opened the scoring in the first leg of their last 16 tie before Jan Vertonghen and Llorente wrapped up a 3-0 win on Spurs’ last European night at Wembley.
Dortmund did all they could to try and make Spurs wilt at Signal Iduna Park, suffocating their visitors in the first half and somehow not finding a way through.
But returning Kane managed to put the tie to bed with an emphatic finish just after half time to ensure Tottenham would advance to the Champions League quarter-finals for the first time in eight years.
‘Auf wiedersehen’ sang the away fans who were finally going back to their spiritual home.
Spurs’ first European game at Tottenham Hotspur Stadium came in the first leg of their last eight tie with Premier League champions Manchester City.
Pep Guardiola’s rotation appeared to have made them a bit jaded, but they were handed a boost when Kane limped off just after the interval.
Once again however, Son took control in the England captain’s absence and found the goal that ensured Spurs took a precious 1-0 lead to the Etihad Stadium.
Raheem Sterling, 4’.
Bernardo Silva, 11’.
Sergio Aguero, 59’.
VAR, no goal, offside, 90+6’.
Even just reading this very basic sequence of events is exhausting. But Tottenham just about did enough to eliminate the favourites to win the Champions League and advance to their first European Cup semi-final since 1962.
Spurs entered the first leg of their semi-final with Ajax with some considerable obstacles to overcome.
Kane and Winks had been ruled out for the rest of the domestic season. Son was suspended. Almost every outfield player had nothing left in the tank after a draining campaign.
An early strike from Donny van de Beek saw Ajax win 1-0 in the capital, meaning Spurs had a very simple remit for the biggest second leg in their history – win.
Son had returned from his suspension and Vertonghen had recovered from his concussion in the first leg. That was good.
Matthijs de Ligt and Hakim Ziyech put Ajax 3-0 up on aggregate. That was bad.
With nothing left to lose, Spurs put in one of the most incredible second-half performances in the history of the European Cup.
Lucas rounded off a pinpoint counter attack to pull one back, before a masterful second followed minutes later to change the whole complexion of a tie that looked comfortably Ajax’s.
Tottenham were on top but remained wildly susceptible to counter attacks, but just when they thought all hope was lost, Alli’s 95th minute flick was met by the left foot of Lucas.
Spurs had reached their first ever Champions League final, against all the odds and cheating death time and time again.
The fine margins and inches which helped Tottenham meet Liverpool in the final weren’t present in Madrid.
Sissoko was harshly adjudged to have handled the ball in his own area almost immediately from kick off and Mohamed Salah’s resulting penalty knocked the stuffing out of Spurs.
Divock Origi killed Tottenham’s dreams of another memorable comeback in the closing stages.
The most heartbreaking defeat in Spurs history? Sure. But at the end of the most thrilling run that perfectly encapsulated Tottenham Hotspur? Absolutely.