Tottenham’s Champions League nights to forget

Tottenham had another night to forget in the Champions League, bowing out to AC Milan.

A limp 0-0 draw at the Tottenham Hotspur Stadium raised further questions about the future of boss Antonio Conte and the Italian’s likely exit might well be expedited after the home fans angrily voiced their disapproval at full-time.

Here, the PA news agency’s Reuben Rosso-Powell looks at five other occasions where Spurs suffered in European football’s premier club competition.

Tottenham 0 Liverpool 2 – final, June 1, 2019

Tottenham’s Eric Dier walks past the trophy after collecting his runner’s up medal after the Champions League Final (PA/Mike Egerton)

Tottenham’s first Champions League final did not go to plan as they fell to Jurgen Klopp’s Liverpool in Madrid.

Moussa Sissoko gave away an early penalty for a handball, which was converted by Mohamed Salah.

The game lacked intensity for most parts but any doubt about the outcome was ended when Spurs goalkeeper Hugo Lloris was unable to save Divock Origi’s strike.

Tottenham 2 Bayern Munich 7 – Group B, October 1, 2019

Serge Gnabry celebrates at full-time after scoring four against Tottenham (PA/John Walton)

Mauricio Pochettino’s side were battered on home turf by Bayern Munich and former Arsenal man Serge Gnabry who bagged four on the night.

Tottenham were competitive in the first half having led the game through Son Heung-min, although goals by Joshua Kimmich and Robert Lewandowski gave Bayern a 2-1 lead going into the break.

The floodgates well and truly opened in the second half as Gnabry scored four times in 35 minutes, before Lewandowski grabbed another. Tottenham’s capitulation was their heaviest defeat in their new stadium.

Real Madrid 4 Tottenham 0 – quarter-final, April 5, 2011

Harry Redknapp’s side crumbled as they conceded four in Madrid (PA/Sean Dempsey)

The opening leg of the 2010-11 quarter-final was miserable for Spurs, who crumbled at the Santiago Bernabeu.

A former Arsenal player again had a hand in the rout, with Emmanuel Adebayor scoring twice after Peter Crouch had been sent off early on for a second bookable offence.

Angel Di Maria and Cristiano Ronaldo sealed the victory and put the tie out of Tottenham’s reach.

RB Leipzig 3 Tottenham 0 – round of 16 second leg, March 10, 2020

Lucas Moura appears dejected after RB Leipzig’s Emil Forsberg scores his side’s third of the game (PA/John Walton)

Trailing 1-0 from the first leg of this last 16 clash, Spurs were torn apart in the return.

Lloris failed to keep out two first-half Marcel Sabitzer efforts which gave the hosts complete control of the tie.

Jose Mourinho’s men failed to respond in the second half and their misery was compounded when Emil Forsberg scored late on.

Tottenham 1 Juventus 2 – round of 16 second leg, March 7, 2018

Paulo Dybala scored as Juventus sent Tottenham out of the Champions League (PA/Nick Potts)

The two sides drew 2-2 in the opening leg and things looked promising for the Premier League team when Son Heung-min opened the scoring in the first half at Wembley.

However, Tottenham’s lack of concentration led to a quickfire Argentinian double through Gonzalo Higuain and Paulo Dybala and Pochettino’s men were unable to overturn the deficit.

Juve captain Giorgio Chiellini rubbed salt in Spurs’ wounds afterwards when he said: “It’s the history of Tottenham…they always miss something.”