History

Every penalty shoot-out involving Chelsea

After Chelsea set two new club records by beating Southampton on penalties, we recall every shoot-out in Blues history…

Our latest victory secured from 12 yards came in last night’s Carabao Cup fourth-round tie against Southampton, as Marcos Alonso, Callum Hudson-Odoi, Ben Chilwell and Reece James all held their nerve to find the net, while Kepa Arrizabalaga continued to impress in shoot-outs by tipping Theo Walcott’s effort onto the post.

That triumph means for the first time in Chelsea history we have won three consecutive penalty shoot-outs, all of which have come in 2020/21 and followed a 1-1 draw in 90 minutes, after our defeat of Aston Villa in the previous round of the Carabao Cup and beating Villarreal to lift the UEFA Super Cup in Belfast.

It is also the first time ever that the Blues have won three penalty shoot-outs in the same season. Given we are only in October and remain active in four knockout competitions – Carabao Cup, FA Cup, Champions League and FIFA Club World Cup – that club record could even be extended further before the end of the campaign.

This latest penalty victory over Southampton came in the 31st competitive shoot-out involving Chelsea and we have a mixed record from the spot, winning 15 of them and losing 16.

The first competition in England to introduce penalty shoot-outs on a permanent basis was the League Cup and it was in that tournament our first experience of the format arrived in 1983, almost a decade before the FA Cup followed suit.

We had done very well to beat Leicester City 2-0 in the away leg of our second-round tie, thanks to goals from Paul Canoville and Kerry Dixon, as they were top division at the time and we were second tier, but the Blues surrendered the lead in the return match at Stamford Bridge. Thankfully, goalkeeper Eddie Niedzwiecki made himself Chelsea’s first shoot-out hero by saving Leicester’s first and last efforts of the five to secure victory.

Unfortunately things didn’t always go so smoothly, as shown when we lost five shoot-outs in a row between 2005 and 2008, including the most painful so far on our first-ever Champions League final appearance.

It was fitting then that we lifted Europe’s most prestigious club trophy for the first time after a shoot-out victory four years later, and for every agonising defeat there is a famous victory from the spot to savour.

We have listed all 31 of Chelsea’s penalty shoot-outs below and picked out a few of the most memorable ones to recall in more detail…

25 October 1983 - Milk Cup second round, second leg
Chelsea 0 Leicester 2 (2-2 on aggregate)
Line-up: Niedzwiecki, Hollins, J Jones, Pates, McLaughlin, Speedie, Canoville, Spackman, Dixon, C Lee, Nevin
Crowd: 15,646
Won 4-3 on penalties after extra time
Penalty scorers: Dixon, C Lee, Hollins, Spackman
Penalty miss: Speedie
Penalty saves: Niedzwiecki 2

13 November 1985 - Full Members Cup area semi-final
West Brom 2 Chelsea 2
Line-up: Niedzwiecki, Wood, Dublin, Pates, Isaac, K Jones (Jasper), Nevin, Spackman, McAllister, Speedie, M Hazard (C Lee)
Scorers: Speedie, McAllister
Crowd: 4,070
Won 5-4 on penalties after extra time
Penalty scorers: Spackman, Pates, Jasper, Wood, C Lee

18 February 1991 - ZDS Cup third round
Chelsea 1 Luton 1
Line-up: Beasant, Clarke, Dorigo, Dickens, Cundy, Monkou, Stuart (K Wilson), Matthew, Dixon, Durie, Le Saux (Hall)
Scorer: Stuart
Crowd: 3,849
Lost 1-4 on penalties after extra time
Penalty scorer: Dorigo
Penalty misses: Durie, Clarke

26 November 1991 - ZDS Cup area quarter-final
Chelsea 2 Ipswich 2
Line-up: Hitchcock, Clarke, Boyd (Allon), V Jones, Elliott, Monkou, Le Saux, Dickens, Dixon, K Wilson (Stuart), Wise
Scorers: Jones, Allon
Crowd: 6,325
Won 4-3 on penalties after extra time
Penalty scorers: Wise, Dixon, Allon, V Jones
Penalty miss: Stuart
Penalty saves: Hitchcock 2

8 February 1995 - FA Cup fourth round replay
Chelsea 1 Millwall 1
Line-up: Kharine; Clarke, D Lee, Sinclair, Minto; Burley, Spackman (Newton), Peacock (Furlong), Wise; Stein, Spencer
Scorer: Stein
Crowd: 25,515
Lost 4-5 on penalties after extra time
Penalty scorers: Stein, Wise, Burley, D Lee
Penalty miss: Spencer

17 January 1996 - FA Cup third round replay
Newcastle 2 Chelsea 2
Line-up: Hitchcock; Duberry, D Lee, Myers (Clarke); Petrescu, Gullit, Newton, Phelan; Wise, Spencer (Peacock); M Hughes (Furlong)
Scorers: Wise (pen), Gullit
Crowd: 36,535
Won 4-2 on penalties after extra time
Penalty scorers: D Lee, Wise, Peacock, Newton
Penalty save: Hitchcock 1

Our first victory in an FA Cup shoot-out came at a time when the competition was causing us plenty of heartache, but a wave of optimism was beginning to flow through Stamford Bridge. We hadn’t lifted the famous old trophy since 1970 and our previous two attempts to put that right had ended in a painful 4-0 defeat to Manchester United in the final followed by a fourth-round exit to London rivals Millwall at home on penalties.

There was a feeling that 1995/96 could be the season to end our jinx, fuelled by the arrival of exciting signings like Ruud Gullit, Mark Hughes and Dan Petrescu, but an injury-time equaliser denied us a home win over Newcastle United in the third round and in the replay we were the ones who needed to come from behind, salvaging a draw from two goals down thanks to Gullit’s strike in the 89th minute.

However, for all the new signings, it was the tried and tested English core of the team that gave us the win in the shoot-out, with David Lee, Gavin Peacock, skipper Dennis Wise (who had also scored from the spot in the second half) and, calmy and decisively, Eddie Newton all finding the net, while Peter Beardsley hit the bar for Newcastle and Kevin Hitchcock kept out Steve Watson, celebrating exuberantly in front of the Chelsea fans despite our opponents still having three penalties remaining. He heard about that from his team-mates afterwards!

Unfortunately, we had another year to wait before we got our hands on the FA Cup for a second time, though, as we eventually lost the 1996 semi-final to Man Utd.

3 August 1997 - Charity Shield
Chelsea 1 Man Utd 1 (Wembley)
Line-up: De Goey; Sinclair, Leboeuf, Clarke, Granville; Wise, Morris (Petrescu), Poyet, Di Matteo; M Hughes (Vialli), Zola
Scorer: M Hughes
Crowd: 73,636
Lost 2-4 on penalties after 90 minutes
Penalty scorers: Zola, Leboeuf
Penalty misses: Sinclair, Di Matteo

15 October 1997 - Coca-Cola Cup third round
Chelsea 1 Blackburn 1
Line-up: Hitchcock; Clarke, Gullit (D Lee), Leboeuf, Granville; Nicholls, Newton (Sinclair), Di Matteo, Babayaro; M Hughes (Hampshire), Vialli
Scorer: Di Matteo
Crowd: 18,671
Won 4-1 on penalties after extra time
Penalty scorers: Leboeuf, Sinclair, Clarke, Nicholls
Penalty save: Hitchcock 1

7 January 1998 - Coca-Cola Cup quarter-final
Ipswich 2 Chelsea 2
Line-up: De Goey; Sinclair (Clarke), Leboeuf, Myers (Gullit), Granville; Di Matteo, Lambourde, Wise, Le Saux; Flo (M Hughes), Zola
Scorers: Flo, Le Saux
Crowd: 22,088
Won 4-1 on penalties after extra time
Penalty scorers: Leboeuf, Zola, Di Matteo, M Hughes
Penalty saves: De Goey 2

In a promising sign for Thomas Tuchel’s men this season, the only previous occasion on which we have won two penalty shoot-outs in the same competition in a single campaign ended with us lifting the trophy at Wembley. That came in the 1997/98 League Cup when one of the most entertaining Chelsea sides ever assembled, fresh from winning the FA Cup the previous season, required penalties to see off Blackburn and Ipswich en route to the final.

Against Blackburn in the third round we were slightly short of firepower by the time it came penalties, with Gianluca Vialli sent off in extra-time and Scottish teenager Steven Hampshire replacing his strike partner Hughes to make his only Chelsea appearance. However, defenders Frank Leboeuf, Frank Sinclair and Steve Clarke all scored to get us off to a great start and Hitchcock saved again, this time from future Blues striker Chris Sutton, allowing Mark Nicholls to net the decisive kick.

Three months later in the quarter-finals, we had a few more attacking options available, as Hughes, Gianfranco Zola and Roberto Di Matteo all hit the back of the net in the shoot-out, although it was set-piece expert Leboeuf who was again entrusted with the first kick. Despite Hitchcock's earlier successes, this time it was Ed de Goey who was guarding our net, and the Dutchman did even better by keeping out two of Ipswich’s three penalties, making it a very one-sided 4-1 win in the shoot-out.

26 October 2005 - Carling Cup third round
Chelsea 1 Charlton 1
Line-up: Cudicini; Ferreira, Huth, Terry, Bridge (Lampard); Geremi, Essien, Gudjohnsen; Wright-Phillips (J Cole), Crespo (Drogba), Robben
Scorer: Terry
Crowd: 42,198
Lost 4-5 on penalties after extra time
Penalty scorers: Robben, Gudjohnsen, Lampard, Drogba
Penalty miss: Huth

1 May 2007 - Champions League semi-final, second leg
Liverpool 1 Chelsea 0 (1-1 on agg)
Line-up: Cech; Ferreira, Essien, Terry, A Cole; Mikel, Makelele (Geremi), Lampard; J Cole (Robben), Drogba, Kalou (Wright-Phillips)
Crowd: 42,554
Lost 1-4 on penalties after extra time
Penalty scorer: Lampard
Penalty misses: Robben, Geremi

5 August 2007 - Community Shield
Man Utd 1 Chelsea 1 (Wembley)
Line-up: Cech; Johnson (Sidwell), Ben-Haim, Carvalho, A Cole (Diarra); Mikel, Essien, Lampard; Wright-Phillips, J Cole (Sinclair), Malouda (Pizarro)
Scorer: Malouda
Crowd: 80,731
Lost 0-3 on penalties after 90 minutes
Penalties missed: Pizarro, Lampard, Wright-Phillips

21 May 2008 - Champions League Final
Man Utd 1 Chelsea 1 (Moscow)
Line-up: Cech; Essien, Carvalho, Terry, A Cole; Ballack, Makelele (Belletti), Lampard; J Cole (Anelka), Drogba, Malouda (Kalou)
Scorer: Lampard
Crowd: 67,310
Lost 5-6 on penalties after extra time
Penalty scorers: Ballack, Belletti, Lampard, A Cole, Kalou
Penalty misses: Terry, Anelka
Penalty save: Cech 1

Every team has their own penalty shoot-out memory which sends a shudder down the spine and is almost too painful to mention, and for Chelsea supporters that undoubtedly came in Moscow in 2008.

We had never reached the Champions League final before, but by the end many were hoping they could erase the memory completely as we were beaten on penalties in an all-English affair with Manchester United.

The shoot-out started well for the Blues, as Petr Cech gave us the advantage by saving from Cristiano Ronaldo, but that was as good as it got. Long-time Chelsea captain John Terry heartbreakingly slipped on the sodden turf and hit the post before Nicolas Anelka was kept out by Edwin van der Sar, extending our wait to become European champions.


12 November 2008 - Carling Cup fourth round
Chelsea 1 Burnley 1
Line-up: Cudicini; Ferreira, Alex, Ivanovic, Bridge (c); Mineiro; Kalou, Belletti (Lampard), Deco (Mikel), Malouda; Drogba (Di Santo)
Scorer: Drogba
Crowd: 41,369
Lost 4-5 on penalties after extra time
Penalty scorers: Lampard, Kalou, Ferreira, Malouda.
Penalty misses: Bridge, Mikel

9 August 2009 - Community Shield
Man Utd 2 Chelsea 2 (Wembley)
Line-up: Cech; Ivanovic (Bosingwa), Carvalho, Terry (c), A Cole; Mikel (Ballack); Essien, Malouda (Deco); Lampard; Anelka (Kalou), Drogba
Scorers: Carvalho, Lampard
Crowd: 85,896
Won 4-1 on penalties after 90 minutes
Penalty scorers: Lampard, Ballack, Drogba, Kalou
Penalty saves: Cech 2

2 December 2009 - Carling Cup fifth round
Blackburn 3 Chelsea 3
Line-up: Hilario; Belletti (Bruma), Ferreira, Ivanovic, Zhirkov; Ballack (c), Mikel, Malouda; J Cole (Drogba), Deco (Kakuta); Kalou
Scorers: Drogba, Kalou, Ferreira
Crowd: 18,136
Lost 3-4 on penalties after extra time
Penalty scorers: Drogba, Malouda, Zhirkov
Penalty misses: Ballack, Kakuta
Penalty save: Hilario 1

19 February 2011 - FA Cup fourth round replay
Chelsea 1 Everton 1
Line-up: Cech; Ferreira, Ivanovic, Terry (c), A Cole; Ramires, Lampard, Mikel (Essien), Malouda (Anelka); Kalou (Zhirkov), Drogba
Scorer: Lampard
Crowd: 41,113
Lost 3-4 on penalties after extra time
Penalty scorers: Lampard, Drogba, Essien
Penalty misses: Anelka, A Cole
Penalty save: Cech 1

21 September 2011 - Carling Cup third round
Chelsea 0 Fulham 0
Line-up: Cech (c) (Turnbull); Ferreira, Alex, David Luiz, Bertrand; McEachran (Terry), Romeu, Malouda; Sturridge (Lampard), Lukaku, Kalou
Crowd: 37,632
Won 4-3 on penalties after extra time
Penalty scorers: David Luiz, Terry, Kalou, Malouda
Penalty misses: Lampard
Penalty save: Turnbull 1

19 May 2012 - Champions League final
Bayern Munich 1 Chelsea 1 (Munich)
Line-up: Cech; Bosingwa, Cahill, David Luiz, A Cole; Mikel, Lampard (c); Kalou (Torres), Mata, Bertrand (Malouda); Drogba
Scorer: Drogba
Crowd: 62,500
Won 4-3 on penalties after extra time
Penalty scorers: David Luiz, Lampard, A Cole, Drogba
Penalty misses: Mata
Pen saves: Cech 2

Given the events in Moscow four years earlier, it’s fair to say there were plenty of nervous faces in the crowd at the Allianz Arena when our next appearance in the Champions League final also went to penalties.

With the spot kicks against Bayern Munich taken at the end holding their supporters in their own stadium, the pressure on the Chelsea players couldn’t have been higher, but it was the Blues who held their nerve. In the reverse of Moscow, we were the ones who started on the back foot after Juan Mata’s miss, but the rest of our takers proved fearless as two club legends emerged as fitting heroes.

Cech saved twice in the shoot-out, from Ivica Olic and Bastian Schweinsteiger, in addition to saving a penalty by former Chelsea team-mate Arjen Robben during extra-time, becoming Bayern’s nemesis on the night.

With David Luiz, Frank Lampard and Ashley Cole all finding the net, that left the decisive moment in the hands of Didier Drogba, who wasn't involved in the shoot-out in Moscow after being sent off. Of course, he tucked his spot-kick away in the bottom corner, sparking wild celebrations on and off the pitch from those wearing Blue as we were finally crowned champions of Europe.

30 August 2013 - UEFA Super Cup
Bayern Munich 2 Chelsea 2 (Prague)
Line-up: Cech; Ivanovic, Cahill, David Luiz, A Cole; Ramires, Lampard (c); Schurrle (Mikel), Oscar, E Hazard (Terry); Torres (Lukaku)
Scorers: Torres, E Hazard
Crowd: 17,686
Lost 4-5 on penalties after extra time
Penalty scorers: David Luiz, Oscar, Lampard, A Cole
Penalty miss: Lukaku

27 October 2015 - Capital One Cup fourth round
Stoke City 1 Chelsea 1
Line-up: Begovic; Zouma, Cahill, Terry (c), Baba (Kenedy); Ramires (Traore), Mikel; Willian, E Hazard, Oscar; Diego Costa (Remy)
Scorer: Remy
Crowd: 24,886 
Lost 4-5 on penalties after extra time
Penalty scorers: Willian, Oscar, Remy, Zouma.
Penalty miss: E Hazard

6 August 2017 - Community Shield
Arsenal 1 Chelsea 1 (Wembley)
Line-up: Courtois; Azpilicueta, David Luiz, Cahill (c); Moses, Fabregas, Kante, Alonso (Rudiger); Willian (C Musonda), Pedro; Batshuayi (Morata)
Scorer: Moses
Crowd: 83,325
Lost 1-4 on penalties after 90 minutes
Penalty scorer: Cahill
Penalty misses: Courtois, Morata

17 January 2018 - FA Cup third round replay
Chelsea 1 Norwich 1
Line-up: Caballero; Ampadu (Christensen), David Luiz, Azpilicueta (c); Zappacosta, Drinkwater (E Hazard), Bakayoko, Kenedy (Kante); Willian, Pedro; Batshuayi (Morata)
Scorer: Batshuayi
Crowd: 39,684
Won 5-3 on penalties after extra time
Penalty scorers: Willian, David Luiz, Azpilicueta, Kante, E Hazard
Penalty save: Caballero 1

24 January 2019 - Carabao Cup semi-final, second leg
Chelsea 2 Tottenham 1 (2-2 on aggregate)
Line-up: Kepa; Azpilicueta (c), Rudiger, David Luiz, Emerson; Kante, Jorginho, Barkley (Kovacic); Pedro (Willian), Giroud, E Hazard
Scorers: Kante, E Hazard
Crowd: 38,610
Won 4-2 on penalties after 90 minutes
Penalty scorers: Willian, Azpilicueta, Jorginho, David Luiz
Penalty save: Kepa 1

24 February 2019 - Carabao Cup final
Chelsea 0 Manchester City 0 (Wembley)
Line-up: Kepa; Azpilicueta (c), Rudiger, David Luiz, Emerson; Kante, Jorginho, Barkley (Loftus-Cheek); Pedro (Hudson-Odoi), E Hazard, Willian (Higuain)
Crowd: 81,775
Lost 3-4 on penalties after extra time
Penalty scorers: Azpilicueta, Emerson, E Hazard
Penalty misses: Jorginho, David Luiz
Penalty save: Kepa 1

9 May 2019 - Europa League semi-final, second leg
Chelsea 1 Eintracht Frankfurt 1 (2-2 on aggregate)
Line-up: Kepa; Azpilicueta (c), Christensen (Zappacosta), David Luiz, Emerson; Kovacic, Jorginho, Loftus-Cheek (Barkley); Willian (Pedro), Giroud (Higuain), E Hazard
Scorer: Loftus-Cheek
Crowd: 36,070
Won 4-3 on penalties after extra time
Penalty scorers: Barkley, Jorginho, David Luiz, E Hazard
Penalty miss: Azpilicueta
Penalty saves: Kepa 2

This season’s three consecutive penalty successes were especially welcome, seeing as they ended an unhappy run of losing three of our previous four shoot-outs. However, that sole victory during that period did help us to lift a trophy, as it arrived in the semi-finals of the 2018/19 Europa League. After back-to-back 1-1 draws across the two legs with Eintracht Frankfurt, penalties were again needed to decide the winner in a continental tie against German opposition.

Just as in Munich, we found ourselves at a disadvantage after Cesar Azpilicueta’s penalty was stopped brilliantly by Kevin Trapp, but then Kepa dramatically swung things in our favour. He had already given us a taste of what he could do with shoot-out saves in that season’s Carabao Cup semi-final and final, and did again by stopping Martin Hinteregger’s shot with his legs and diving low to his right to deny Goncalo Pacienca.

That saw us go from 3-2 down to drawing 3-3, with all of Eintracht’s kicks taken and Eden Hazard stepping up with the chance to decide the game with the final shot of the regulation five. Needless to say the Belgian made no mistake, calmly sending the keeper the wrong way to book our place in the final against Arsenal.

14 August 2019 - UEFA Super Cup
Liverpool 2 Chelsea 2 (Istanbul)
Line-up: Kepa; Azpilicueta (c), Christensen (Tomori), Zouma, Emerson; Kante, Jorginho, Kovacic (Barkley); Pedro, Giroud (Abraham), Pulisic (Mount)
Scorers: Giroud, Jorginho (pen)
Crowd: 38,434
Lost 4-5 on penalties after extra time
Penalty scorers: Jorginho, Barkley, Mount, Emerson
Penalty miss: Abraham

29 September 2020 - Carabao Cup fourth round
Tottenham 1 Chelsea 1
Line-up: Mendy; Azpilicueta (c), Tomori, Zouma, Chilwell (Emerson); Jorginho, Kovacic (Kante); Hudson-Odoi, Mount, Werner; Giroud (Abraham)
Scorer: Werner
Crowd: Behind closed doors
Lost 4-5 on penalties after 90 minutes
Penalty scorers: Abraham, Azpilicueta, Jorginho, Emerson
Penalty miss: Mount

11 August 2021 - UEFA Super Cup
Villarreal 1 Chelsea 1 (Belfast)
Line-up: Mendy (Kepa); T Chalobah, Zouma (Christensen), Rudiger; Hudson-Odoi (Azpilicueta), Kante (c) (Jorginho), Kovacic, Alonso; Ziyech (Pulisic), Werner (Mount), Havertz
Scorer: Ziyech
Crowd: 10,435
Won 6-5 on penalties after 90 minutes
Penalty scorers: Azpilicueta, Alonso, Mount, Jorginho, Pulisic, Rudiger
Penalty miss: Havertz
Penalty saves: Kepa 2

22 September 2021 - Carabao Cup third round
Chelsea 1 Aston Villa 1
Line-up: Kepa; James, T Chalobah, Sarr; Hudson-Odoi, Kante (c) (Mount), Loftus-Cheek, Saul (Barkley), Chilwell; Ziyech (Lukaku), Werner
Scorer: Werner
Crowd: 39,852
Won 4-3 on penalties after 90 minutes
Penalty scorers: Lukaku, Mount, Barkley, James
Penalty miss: Chilwell
Penalty save: Kepa 1

26 October 2021 - Carabao Cup fourth round
Chelsea 1 Southampton 1
Line-up: Kepa; James, T Chalobah, Sarr; Hudson-Odoi, Kovacic, Saul, Alonso (c); Ziyech (Mount), Havertz, Barkley (Chilwell)
Scorer: Havertz
Crowd: 39,766
Won 4-3 on penalties after 90 minutes
Penalty scorers: Alonso, Hudson-Odoi, Chilwell, James
Penalty miss: Mount
Penalty save: Kepa 1

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