It was almost four years ago, but Tottenham’s journey to the Champions League final in 2019 feels like a distant memory.
Spurs have been trying to emulate, or even surpass that level of achievement in the following years but a dour 1-0 aggregate defeat against AC Milan on Wednesday means that they’ll have to wait for another bite of the cherry.
Pochettino’s side were so close to going all the way in the 2019 Champions League final
It was Liverpool who came out victorious in Madrid
With supporters feeling downbeat about their team under Antonio Conte, fans can only dream of having a side with the quality and character to make it all the way to a cup final in 2019, let alone the biggest prize of all.
Mauricio Pochettino’s side certainly didn’t have it easy either as they finished second in a group containing Barcelona, Inter Milan and PSV Eindhoven before seeing off Borussia Dortmund in the round of 16.
What followed were two heroic aggregate victories over Manchester City and Ajax, meaning that their spot in the showpiece event was richly deserved.
While the contest with fellow English side Liverpool ultimately went the way of Jurgen Klopp’s side, the matchday squad who featured at the Wanda Metropolitano will go down as one of the best in Tottenham’s history.
So where are the 14 players who made it onto the pitch against the Reds? TalkSPORT.com takes a look…
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Tottenham starting XI
The veteran goalkeeper was a key player for Tottenham back in 2019 and captained the team in Madrid.
While it was an evening that ended in disappointed, the 36-year-old will always be remembered as the man to lead Spurs out in the biggest match in European football.
Still with Tottenham, Lloris will be hoping that he might get one more opportunity to do so again.
Lloris is still the main man between the sticks with at Tottenham
The England international was Mauricio Pochettino’s first choice right-back during the 2018/19 campaign and played a big role in the club’s journey to the final.
Trippier clearly took a liking to life in Madrid with the Champions League final proving to be his final match with Spurs before joining Atletico that summer.
Now captain of Newcastle United, he’ll be hoping to be leading his new club out in the Champions League next season as they challenge Spurs for fourth spot in the league.
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Trippier’s last game for Tottenham was in the Champions League final with Liverpool
The Belgian star was a hugely popular figure in north London and it was his towering displays that helped Spurs to almost go all the way.
Forging a powerful partnership with Jan Vertonghen, Alderweireld spent six years at the heart of Tottenham’s defence before moving on in 2021.
Now with Royal Antwerp in his native Belgium, the 34-year-old will always be remembered as one of Tottenham’s star performers.
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Alderweireld was a key man for Spurs for many years under Pochettino
Another player who played a massive role in Tottenham’s journey to the final, especially a match-winning Wembley display against Dortmund in an unfamiliar left wing-back role.
Vertonghen was Spurs’ vice-captain during that campaign but stuck around in north London for just 12 months more before moving on to Benfica.
Still playing at the age of 35, the defender now plays for Anderlecht after joining in September 2022.
Vertonghen was a key leader for Pochettino
The former England international was once regarded as one of the best left-backs in Europe, a status that he held due to his dominance for Spurs.
Unfortunately things went south for him once Mauricio Pochettino left the club in 2019, with Rose falling out of favour under Jose Mourinho.
Despite a successful loan spell with Newcastle, Rose found himself playing for Watford for the 2021/22 campaign, with the ex-England international being without a club since.
Rose was a top-level left-back before his career unraveled under Jose Mourinho
The midfielder had a hit and miss spell under Pochettino after joining Tottenham from Newcastle in 2016.
After struggling initially, a role in central midifield suddenly changed his career around in north London.
Unfortunately, it was a handball from Sissoko that let to Spurs going behind just 22 seconds into the final with Liverpool, sending them on the way to defeat.
After moving to join Watford in 2021, Sissoko now plays for French club Nantes after joining last summer.
Sissoko started in the middle of the park against Liverpool in Madrid
A product of Tottenham’s academy, it was a dream for Winks to start for his hometown club in the Champions League final.
The midfielder partnered Sissoko in the engine room and earned a five-year contract with the club in the aftermath of the defeat.
Since then, Winks has continued to feature for Spurs but joined Sampdoria on a season-long loan with an option for the deal to become permanent.
Winks was a huge favourite under Pochettino but under Conte is in the shadows
Back in 2019, Alli was regarded as one of the best young midfielders in the world, but since that Champions League final, things have derailed in spectacular fashion.
After falling out of favour with Spurs, the midfielder joined Everton in January 2021 but once again, struggled to meet expectations.
Now on a season-long loan deal with Besiktas, the 26-year-old got off to a stuttering start to life in Turkey, but has since showed early signs of showcasing his true quality once again.
Alli had the world at his feet when playing under Pochettino at Spurs
The Danish star was the beating heart of Pochettino’s Tottenham side, meaning that it was a real blow when he joined Inter Milan in January the next year.
After suffering a cardiac arrest with Denmark at the Euros in 2021, Eriksen was forced to rebuild his career and did so with an impressive short-term spell with Brentford last year.
Such was the level of his performances, the Denmark star earned a move to Manchester United where he’s using his experience to aid Erik ten Hag’s side in their newfound search for glory.
Eriksen was the beating heart of Tottenham’s Champions League final team
The South Korean star was a key man for Tottenham four years ago. scoring four goals in 12 matches in the Champions League.
While Son was unable to score the goals needed to get Spurs over the line that day, he’s certainly made up for it in the years since.
Still just 30, Son has now scored 140 goals in 360 appearances for the club and will be desperate to add more goals to that tally in the years to come.
Son was distraught not to come out victorious in Madrid
Tottenham’s biggest talisman, Kane was distraught not to win the Champions League final, particularly given the extended trophy drought that has followed.
Since then Kane has gone on to become Spurs’ all-time top goalscorer after passing Jimmy Greaves’ record, but what he really craves is silverware.
It remains to be seen whether he’ll get his wish at Tottenham, or if that night in Madrid will go down as the biggest missed opportunity of his decorated career.
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Kane looked downbeat as he made his way past the Champions League trophy
Tottenham’s first change on the night was the man who led them to victory in the semi-final thriller with Ajax.
The Brazilian enjoyed his best season in a Spurs shirt in 2018/19 with 15 goals to his name, as well as the sort of performances that established him as a cult hero at the club.
Still with Tottenham, Moura’s days in north London look to be numbered but his heroics in the Champions League semi final will never be forgotten.
Moura was the hero as Tottenham saw off Ajax in the Champions League semi final
The defender was brought off the bench in the second half in Madrid, but couldn’t help his side to victory.
While Dier has been with Spurs since 2014, he’s seen his role at the club questioned on numerous occasions, however he continues to be a key player under Antonio Conte.
But with a contract that expires in 2024, it remains to be seen if the 29-year-old will still stay at the club long-term.
Dier is still a key player for Tottenham
A player who was very much Harry Kane’s understudy at Spurs, Llorente certainly made his impact during their journey to the Champions League final.
The powerful Spaniard scored what turned out to be the winning goal against Manchester City in the quarter-finals, before coming off the bench in the final to try and force Spurs back into the tie.
However it wasn’t to be for the 38-year-old who announced his retirement in February this year after a spell in Spain with Eibar.
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Llorente saw off Manchester City on the road to Madrid
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