Having made a disastrous start to the competition, with one point from their opening three group stage matches, Spurs recovered to advance as runners-up in Group B.
And following successive knockout round victories against Borussia Dortmund and Manchester City, they produced a remarkable comeback against Ajax to book a place in the final on June 1st.
Here we examine how the current crop made history ahead of the Champions League final shown exclusively live on BT Sport.
Inter Milan 2-1 Tottenham
Group B Matchday 1 - September 18th 2018
Tottenham got off to the worst possible start after being drawn into a nightmare group featuring Barcelona, Inter Milan and PSV Eindhoven.
Mauricio Pochettino’s men enjoyed the better of the first half action with only Harry Kane’s hesitation and some smart saves from Samir Handanovic preventing them heading into the interval a goal to the good.
And they drummed home that advantage eight minutes into the second period when Christian Eriksen’s attempt deflected off Miranda and looped horribly over the Inter goalkeeper.
It wasn’t to last. Inter captain Mauro Icardi rifled in a stunning volley from outside the box with five minutes to play before Matias Vecino found himself in the right place at the right time to nod home the winner from a corner at the death.
Pandemonium in Milan but devastation for Tottenham as they made a tricky task even harder with a damaging defeat.
Tottenham 2-4 Barcelona
Group B Matchday 2 - October 3rd 2018
Tottenham and Barcelona played out a pulsating enconter on a patchy Wembley turf with the mercurial Lionel Messi leading the way in London.
It took just two minutes for Barcelona to take the lead when Philippe Coutinho ruthlessly fired home following Messi’s pinpoint through ball.
And Ivan Rakitic doubled Barcelona’s advantage before the half-hour mark with a stunning half-volley from outside the box. Tottenham’s defenders were slow to get out to him but the Croatian’s finish was lethal.
Kane dragged back into the game with a smart finish in the second period but three minutes later Messi tucked home following a one-two to make it 3-1 to the home side.
A deflected Erik Lamela strike gave Spurs another lifeline but at the death Messi made sure of the result, calmly tucking home when afforded space in the Tottenham penalty area. Spurs were now left with a mountain to climb.
PSV 2-2 Tottenham
Group B Matchday 3 - October 24th 2018
In what was billed as a must-win match in Eindhoven, Spurs were caught out when Toby Alderweireld’s horrible error allowed Hirving Lozano to score for the home side.
Davinson Sanchez was denied a leveller by the linesman’s flag but the equaliser eventually came when Lucas Moura thrashed Kieran Trippier’s cut-back into the net.
And a first win of the campaign for Tottenham was in sight when Kane peeled off his marker and nodded home Eriksen’s cross at the back post.
Tottenham almost added a third but were denied by first Jerome Zoet’s save and then the crossbar but a moment of madness at the other end soon cost Pochettino’s men.
Hugo Lloris came charging out of his area to meet a through ball but clattered Lozano, earning a red card in the process.
The 10 men of Tottenham held out until the 87th minute when Luuk de Jong poked home the leveller for PSV – themselves in desperate need of a result.
Tottenham 2-1 PSV
Group B Matchday 4 - November 6th 2018
With one point from their opening three matches, Tottenham’s chances of making the knockout stages were looking slim.
At home to PSV, theoretically the weakest team in the group was a must, must-win and the pressure on Spurs was huge ahead of the Wembley clash.
But like their previous home match against Barcelona, Spurs made a disastrous start when De Jong thumped home a header inside the first minute.
It looked not to be Spurs’ night when Zoet made a stunning double save to deny Eriksen and Dele Alli but Kane’s smart finish 13 minutes from time gave the home side hope.
And Tottenham’s talisman came up trumps yet again in the 88th minute when Kane’s deflected header sealed a 2-1 win and kept Spurs alive in Europe.
Tottenham 1-0 Inter Milan
Group B Matchday 5 - November 28th 2018
With Barcelona top on 10 points after four games and Inter second on seven points, Tottenham on four points needed a result against the Italians at Wembley.
But Luciano Spalletti’s side arrived ready to defend in the oldest of Italian football traditions, looking to frustrate Tottenham from the outset.
Tottenham were the thrusting force in the tie but a combination of Alli, Kane and Lucas Moura missed chances while Harry Winks struck the bar from long range.
Milan Skriniar agonisingly failed to make proper contact six yards out from goal at the other end but the decisive moment came 10 minutes from time as Tottenham finally broke Inter’s resolve.
A speedy counter-attack found Moussa Sissoko and then Alli, the Englishmen teeing up the onrushing Eriksen to smash past Handanovic and secure a huge three points for Pochettino’s men.
Barcelona 1-1 Tottenham
Group B Matchday 6 - December 11th 2018
It was in Tottenham’s hands - win and they advance. But in their way stand the might of Barcelona at the Nou Camp, even if the Spaniards had already qualified.
But for the third time in six games Spurs conceded in the opening eight minutes in the Champions League through a lethal counter-attack.
Tottenham saw a free-kick cleared as far as Kyle Walker-Peters but Ousmane Dembele pounced on the full back, forcing him into an error before charging down the field and finishing brilliantly.
It was another awful start but there was welcome news from Milan as Lozano’s goal for PSV had Inter behind after 13 minutes at the San Siro.
Son Heung-min spurned a great opportunity for Spurs when he fired straight at Jasper Cillessen and for the home team Coutinho was denied only by the post.
But it was a Spurs onslaught as they laid siege to Barcelona’s under-strength side. The usually collected Kane smashed wildly over the bar when put through on goal before Cillessen made a smart stop to deny Eriksen from close range.
Lucas Moura was denied by another brilliant save and when Icardi levelled for Inter in Milan, Tottenham were crashing out of the competition.
Cue another late salvation for Tottenham, this time from Lucas Moura. The Brazilian firing home from close range to send the away supporters into pandemonium and Spurs into the last 16.
Tottenham 3-0 Borussia Dortmund
Last-16 first leg - 13th February 2019
Drawn against Bundesliga leaders Borussia Dortmund in the last-16, Tottenham were handed a daunting task to make it to the quarters.
But after a tense first half in which Dortmund enjoyed the better of the chances, Spurs stepped up to the occasion at Wembley.
Jan Vertonghen, deployed in the unfamiliar position of left-wing back swung a brilliant cross into Son’s path two minutes into the second half and the in-form striker made no mistake.
Vertonghen then gave Tottenham real command of the tie eight minutes from time when he thumped home Serge Aurier’s cross to cap off a brilliant display.
And it got even better as Fernando Llorente nodded home from Eriksen’s corner to leave Tottenham with one foot in the quarter-finals ahead of the return leg in Germany.
Borussia Dortmund 0-1 Tottenham
Last-16 second leg - 5th March 2019
Tottenham’s 3-0 win at Wembley meant Dortmund had a mountain to climb to reach the last eight so they understandably applied the pressure in the opening stages in search of a foothold.
Only a last-ditch Vertonghen tackle denied Marco Reus before the German was kept out by a smart Lloris save, who reacted well to bat away a deflected shot.
Son then almost put the tie beyond any doubt but fired wide of the post before Lloris produced a string of smart saves from Jadon Sancho, Julian Weigl and Reus again to deny Dortmund a lifeline.
And three minutes into the second half Tottenham made Dortmund pay for their profligacy. Kane, put through by Sissoko, lashed home to extinguish German hopes.
Having looked set for a group-stage exit, Tottenham were into the Champions League quarter-finals.
Tottenham 1-0 Manchester City
Quarter-final first leg – April 9th 2019
With Tottenham, Liverpool, Manchester United and Manchester City all in the quarter-finals it seemed inevitable the draw would serve up an all-English tie.
It duly came – with Tottenham and defending Premier League champions City pitted against each other while Liverpool drew Porto and United took on Barcelona.
And the occasion was played out in the surroundings of Tottenham’s shiny new ground – the first European match at the Tottenham Hotspur Stadium.
The first big moment came in the form of a VAR review, when Raheem Sterling’s shot struck Danny Rose’s arm inside the area. After a lengthy delay, Bjorn Kuipers pointed to the spot.
But the usually lethal Sergio Aguero was found wanting as Lloris made a diving save to keep the Argentine’s effort out.
Kane nearly opened the scoring at the other end but Ederson denied the Spurs striker’s effort on the turn. There was soon bad news for the England captain when he was forced off injured having clattered into Fabian Delph.
All that was forgotten 12 minutes from time. Eriksen played in Son behind the defence, the South Korean was forced wide but cut back inside and drilled his effort past Ederson and in. Advantage Tottenham against the favourites City.
Manchester City 4-3 Tottenham
Quarter-final second leg – April 17th 2019
A modern classic played out between two of Europe’s most exciting attacking teams with a huge dollop of controversy at the death.
It looked almost instantly to be City’s night at the Etihad when Sterling curled home a sumptuous effort past Lloris after four minutes.
Yet just three minutes later and the irrepressible Son responded when Aymeric Laporte’s clearance fell to him to lash home via Ederson’s leg.
And with just nine minutes on the clock the South Korean continued his dream campaign with his third goal of the tie, bending home to finish off a swift counter-attack with City’s defence all at sea.
Incredibly, City struck back just a minute later. Bernardo Silva tucking home via a deflection off Rose to bring the home side level on the night. “Have you ever seen a start like this in the Champions League?” cried BT Sport commentator Darren Fletcher.
Sterling then popped up to score his second and City’s third of the night in the 21st minute, scoring from Kevin De Bruyne’s cross to put his side 3-2 up but behind on away goals.
Lloris produced a marvellous stop to keep De Bruyne’s shot out but the Belgian soon made Tottenham pay just before the hour mark.
His surge forward released Aguero who this time made no mistake, lashing home to put City 4-3 up on aggregate and on course for the semi-finals.
The tie took yet another twist as Fernando Llorente bundled home from a corner, the goal subject to a VAR review but the cross was deemed to have come off the Spaniard’s thigh rather than his arm.
Cue a City siege as they searched desperately for a European lifeline with time ticking away. Deep into injury time it looked to have arrived.
The ball broke to Aguero, who teed up Sterling to cut inside and fire past Lloris in the Tottenham goal. City’s celebrations were unbridled, Pep Guardiola going crazy on the touchline and Spurs players left heartbroken on the turf.
But there was one final twist in the tale left. VAR would rule the goal out for offside and the Etihad was left in a stunned silence. Tottenham’s passage to the semi-finals was complete.
Tottenham 0-1 Ajax
Semi-final first leg – April 30th 2019
Europe’s surprise package showed just how they had overcome holders Real Madrid and experienced-campaigners Juventus to reach the final four.
With their swashbuckling, attack-minded style on show from the off they made the most of the hosts lack of cutting edge in front of goal.
With Kane still injured and Son suspended, picking up a booking in the last match at the Etihad Stadium, Spurs were missing their two top scorers and it showed.
Donny van de Beek struck low beyond Lloris in the 15th minute to grab Erik ten Hag's an all-important away goal and despite a second-half improvement from the north London side it was actually the visitors then went closest to a second on the night.
David Neres struck the inside of the post after the interval but thankfully for most in attendance the ball flew back out and it meant Spurs just had to win in Amsterdam to progress.
The game was in-part overshadowed by an injury suffered by the hero of the home tie against Dortmund, Jan Vertonghen. He clashed with team-mate Toby Alderweireld and Ajax goalkeeper Andre Onana and suffered a facial injury.
Despite trying to re-enter the fray, the Belgian defender was clearly shaken up and had to depart within seconds of coming back onto the pitch, this time with the help of two Tottenham staff members.
Ajax 2-3 Tottenham
Semi-final second leg – May 9th 2019
Having seen Liverpool overcome a 3-0 deficit against Barcelona and book their place in the final the night before, Spurs were given hope of upsetting the odds.
But when a towering fifth-minute header by 19-year-old Ajax captain Matthijs de Ligt doubled the hosts advantage even the most hopeful of fans must have doubted.
The returning Son gave the away side more potency in attack and the South Korean hit the post before Hakim Ziyech doubled Ajax's lead on the night.
With nothing to lose Pochettino threw caution to the win and introduced Llorente for holding midfield Victor Wanyama at the break.
Boy did that pay off.
Inspired by Moura, Spurs went on to produce one of the most remarkable comebacks in Champions League history and reach the final for the first time in their history.
The Brazilian scored a quick-fire double before the hour mark to level the scores on the night and those in green knew one more would see them through on away goals.
Vertonghen, who passed all the medical tests he faced after the first leg, almost got the vital goal but his header cannoned back off the bar.
But Moura would not be denied his hat-trick arrowing in a left-foot shot into the bottom corner with virtually the last kick of the game to send Spurs to Madrid on 1st June.
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