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Tottenham’s greatest ever night: 5 best UCL semi-final matches of all time

Photo by Tom Jenkins
Photo by Tom Jenkins
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Manchester City v Real Madrid Semi Final Leg One - UEFA Champions League
Photo by David Ramos/Getty Images

The UEFA Champions League semi-finals have arrived, and in the first match between Manchester City and Real Madrid, we might already have a classic on our hands.

A 4-3 win for Pep Guardiola’s side was regarded by many as one of the most entertaining and dramatic matches this year and arguably one of the great Champions League semi-final fixtures of the last few years.

The game had everything from incredible goals, fantastic pieces of skill and Karim Benzema being Karim Benzema. And with the second-leg set to take place next week, there’s no telling who will win their spot in the final between City and Madrid.

Indeed, both sides will be desperate to book a place in May’s Championship match in Paris, and here at HITC Sport, we look at five other memorable semi-final encounters in Europe’s elite competition, a list that City and Madrid’s match will no doubt make in future years.

Juventus 2-3 Manchester United (1999)

Champs League SF Roy Keane
21 Apr 1999: Manchester United captain Roy Keane wheels away after scoring in the UEFA Champions League semi-final second leg match against Juventus at the Stadio delle Alpi in Turin, Italy. United won 3-2 on the night to go through 4-3 on aggregate. Mandatory Credit: Allsport UK /Allsport

Only one English club has ever won THE Treble consisting of the Premier League, FA Cup and Champions League, and that side was none other than the great Manchester United side of 1998/99, yet this astonishing accolade almost didn’t happen.

Heading in the second leg against Juventus in Turin at 1-1, the Italians took a two-goal lead inside the first 11 minutes. However, United’s never-say-die spirit came out in full force this evening, with Roy Keane putting in arguably his finest ever European display, despite getting suspended for the final, as Sir Alex Ferguson’s side thought their way back to a 3-2 win.

The rest, they say, is history.

Real Madrid 0-2 FC Barcelona (2011)

Real Madrid v Barcelona - UEFA Champions League Semi Final
Photo by Kaz Photography/Getty Images

The early 2010s was arguably the period where Real Madrid and FC Barcelona, in terms of star power, were at their peak in the past 15 years, and when the two sides met in the Champions League semi-final, sparks flew, and then some.

Whilst not many people remember the second leg, the first was an incredible contest as Lionel Messi scored two late goals at the Bernabeu to essentially book Barcelona’s place in the final, with his slalom wonder-goal past the Madrid defence still one of the best in Champions League history.

Borussia Dortmund 4-1 Real Madrid (2013)

FUSSBALL INTERNATIONAL CHL HALBFINALE 12/13: Real Madrid - Borussia Dortmund
Photo by Pressefoto Ulmerullstein bild via Getty Images

Madrid were back in the semi-finals two years later, this time facing a Borussia Dortmund side that had grown over the years as a favourite amongst football hipsters and tactic buffs. Yet their first leg against Los Blancos would change that forever.

A four-goal haul for Robert Lewandowski put both the Polish international and Dortmund right back on the footballing map, and whilst the German side went on to lose the final against Bayern Munich, their Champions League semi-final romp against Madrid is arguably one of the club’s greatest ever results.

Liverpool 4-0 FC Barcelona (2019)

Alexander-Arnold
Photo by TF-Images/Getty Images

Comebacks in the Champions League have become more commonplace this season with the abandonment of the away goals ruling, yet one of the greatest ever before the change came in 2019, when Anfield got the better of Barcelona on a historic night for Liverpool.

With key players out missing and a 3-0 deficit to overturn, Liverpool looked dead and buried to Barcelona, but Divock Origi had other plans, with the Belgian bagging a brace along with Georginio Wijnaldum, who came on at half-time to change the game for the Reds.

Tottenham 3-2 Ajax (2019)

tottenham-hotspur-winger-lucas-moura-celebrates-scoring-against-ajax-champions-league-semi-final-2019-premier-league-gossip
Photo by VI Images via Getty Images

Liverpool’s comeback against Barcelona was bombastic, unprecedented, and made totally irrelevant 24 hours later when Tottenham somehow managed to complete an even more ludicrous result away to Ajax.

Losing 2-0 and 3-0 down on aggregate heading into the 55th minute, Tottenham’s dream run to a first-ever Champions League final looked all but dead, yet two quick-fire goals from Lucas Moura and then a 96th-minute winner from the Brazilian shocked Ajax and the footballing world as Spurs arguably had their greatest ever night in their history.