8 Times Jose Mourinho Lost on Penalties As Sevila Beat Roma To Win Europa League

Jose Mourinho’s penalty record since he became a top-tier manager 23 years ago is dreadful.

The Portuguese tactician's latest spot-kick woes came as AS Roma failed to win the Europa League on Wednesday night, thanks to Sevilla.

Paulo Dybala's first-half strike looked to be enough to hand the Giallorossi their first Europa League title, until Gianluca Mancini's own goal gifted the Andalucians a second-half equaliser.

The tie was decided on penalties after a goalless period of extra-time, with Roger Ibanez's spot kick hitting the post and Sevilla goalkeeper Yassine Bounou saving Mancini's 12-yard effort, the Guardian reported.

According to the Daily Star, the defeat means Mourinho has lost eight out of the nine penalty shootouts he's been involved in as a manager since he started his first-class coaching career with Benfica in 2000.

Chelsea 4-5 Charlton

League Cup, October 2005

During this cagey encounter, Chelsea were leading the Premier League, and Charlton were in second place.

After extra time, the game finished 1-1, and Chelsea kicked first, which was converted by John Terry. Robert Huth was second for Chelsea and he missed.

While Eidur Gudjohnsen, Frank Lampard, and Didier Drogba all scored for Chelsea, the shooters for Charlton— Matt Holland, Hermann Hreidarrson, and Bryan Hughes— also scored to give Charlton the victory.

Under Mourinho, Chelsea had gone 15 months without losing at home; he would claim the record still stood. However, nobody anticipated a German player to miss the penalty kick.

Liverpool 4-1 Chelsea

Champions League, May 2007

Daniel Agger scored the only goal of the semi-final clash to make it 1-1 on aggregate and take it to spot-kicks.

After Xabi Alonso, Lampard, and Steven Gerrard scored, Geremi Njitap, who had been Chelsea's best penalty-taker all season in training, missed from 12 yards to hand Rafael Benitez's side the victory.

Chelsea 0-3 Manchester United

Community Shield, August 2007

After another 1-1 draw in the first game at the newly-opened Wembley, this was Mourinho’s penalty nadir.

Edwin Van der Sar saved Claudio Pizarro’s kick. The Dutchman then went on to save Frank Lampard and Shaun Wright-Phillips’s penalties.

Rio Ferdinand, Michael Carrick, and Wayne Rooney sealed a rare 3-0 score-line in the shoot-out for the Red Devils.

Inter Milan 6-5 AS Roma

Supercoppa Italia final, August 2008

Mourinho slammed for using ugly tactics after he qualifies for another European final

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This was Mourinho’s first, and to date only, shoot-out victory in his professional career.

The 60-year-old thought that Mario Balotelli had won the game against Coppa Italia winners Roma with an 83rd-minute goal to put Inter Milan 2-1 up.

Roma took the lead and scored their first four goals. Zlatan Ibrahimovic and Balotelli both scored from the spot for Inter.

When Dejan Stankovic, who was third up, missed, Francesco Totti was left to make the game-winning kick for Roma.

He struck the crossbar, and it went to sudden death. David Pizarro and Luis Jimenez scored; then Juan missed and Inter skipper Javier Zanetti scored to hand victory to Inter.

Real Madrid 1-3 Bayern Munich

UEFA Champions League, April 2012

Real Madrid won the match 2-1, leaving the tie 3-3 on aggregate against Bayern Munich. In the match, both Cristiano Ronaldo and Arjen Robben had scored from the spot, and it was a surprise that Robben was not one of Bayern’s five nominated kickers.

Instead, David Alaba got them off to a flier and Ronaldo then failed from 12 yards. Mario Gomez then scored and Kaka, a second-half substitute for Angel Di Maria, missed. Bayern were 2-0 up but almost faltered when Toni Kroos and Philipp Lahm failed. Xabi Alonso scored and when Sergio Ramos fired high and wide, Bastian Schweinsteiger scored the fifth and final kick to seal victory for Bayern.

Chelsea 4-5 Bayern Munich

UEFA Super Cup, August 2013

This was Mourinho’s first match back as Chelsea coach and it came against a Bayern side coached by his nemesis from Spain, Pep Guardiola. It was almost a carbon copy of the 2012 Champions League final: a thrilling 2-2 draw in which Bayern had the momentum from scoring an injury-time equaliser through Javi Martinez.

Bayern kicked first and all five players scored: Cech got a hand to Xherdan Shaqiri’s effort, the fifth one, but couldn’t stop it. The first four scored for Chelsea, including Ashley Cole off the inside of the post. Then up stepped Lukaku, looking nervous.

Left-footed, he took a slow run-up and waited a beat for Manuel Neuer to commit himself before he shot. Neuer stayed still, and Lukaku struck the ball weakly to Neuer’s left. The keeper gathered it easily, and Chelsea lost. Lukaku never kicked a ball for Chelsea again that season – he was loaned to Everton one week later.

Stoke 5-4 Chelsea

League Cup, October 2015

After winning the Premier League the previous season, Mourinho's miserable 2015/16 campaign took another turn for the worse as Chelsea were knocked out of the League Cup by Stoke in a penalty shootout.

Stoke took the lead through Jon Walters, but Loic Remy drilled in an injury-time equaliser to send the game to penalties.

Potters' keeper Jack Butland was the hero for the home side, saving the Belgian's high effort to put Stoke into the quarter-finals.

Man United 7-8 Derby

League Cup, September 2018

Derby County beat Manchester United 8-7 in a dramatic penalty shootout to settle a pulsating Carabao Cup tie at Old Trafford and send the Championship club through to the fourth round.

After 15 successful penalties, Rams' goalkeeper Scott Carson saved Phil Jones' effort low to his left to secure a famous victory for Frank Lampard's side.

The result piled the pressure on Mourinho, who was sacked by United three months later.

Tottenham 2-3 Norwich

FA Cup, March 2020

Mourinho's Tottenham Hotspur were dumped out of the FA Cup on penalties by Norwich after missing three spot-kicks in the shootout, losing 3-2 after a 1-1 draw in normal time.

Jan Vertonghen opened the scoring for Spurs following a Giovani Lo Celso set-piece, but Josip Drmic bundled home to take the game to extra-time.

When McLean missed Norwich's first penalty, Spurs were odds-on to progress, but woeful spot-kicks from Troy Parrott, Erik Lamela, and Gedson Fernandes meant visiting Tim Krul was the hero for the visitors.