Twice the charm – League Cup 1997/98

On the road to our League Cup victory against Middlesbrough in the 1998 final, Chelsea were twice taken to penalties, by Blackburn Rovers in the third round and Ipswich Town in the quarter-finals.

Following a 1-1 draw with Rovers at the Bridge in October 1997, the Blues prevailed 4-1 in the shoot-out as Frank Lebouef, Frank Sinclair, Steve Clarke and Mark Nicholls were successful from the spot after Kevin Hitchcock had saved Chris Sutton’s attempt and Lars Bohinen fired over the crossbar.

Ruud Gullit’s side then blew a two-goal lead in 2-2 draw at Ipswich in the last eight. However, Ed de Goey denied James Scowcroft and Mauricio Taricco while Leboeuf, Gianfranco Zola, Roberto Di Matteo and Mark Hughes were all on target in another 4-1 success.

Returning to winning ways – Community Shield 2009

After the win against Ipswich in January 1998, Chelsea suffered five straight shoot-out defeats over the next 11 years including heart-breaking Champions League losses in the 2007 semi-finals to Liverpool and 2008 final against Manchester United.

The barren run thankfully came to an end when we met United in the curtain-raiser to the 2009/10 season. Wayne Rooney’s stoppage time equaliser denied the Blues in regulation but the Red Devils couldn’t make the most of their reprieve as Petr Cech thwarted Ryan Giggs and Patrice Evra while Frank Lampard, Michael Ballack, Didier Drogba and Salomon Kalou were all clinical from 12 yards.

That victory set the tone for a magnificent campaign for Carlo Ancelotti’s side who clinched the Premier League and FA Cup Double for the first time in club history.

Joy at the Bridge – Europa League 2019

After winning 11 of 12 matches on our run to the Europa League semi-finals in 2018/19, the Blues were given a stern test by Eintracht Frankfurt with penalties required after both legs were drawn 1-1.

It was our third shoot-out of the season after we had beaten Tottenham Hotspur in the semi-finals and lost to Manchester City in the final of the Carabao Cup but things didn’t start too well when the Blues; second attempt by Cesar Azpilicueta was saved by Kevin Trapp.

However, Kepa Arrizabalaga (not for the last time) produced two stops in the shoot-out, using his legs to keep out a shot driven straight down the middle by Martin Hinteregger before plunging to his right to deny Goncalo Paciencia. It set the stage for Eden Hazard on his last Chelsea appearance at Stamford Bridge to fire home and seal our place in the final against Arsenal.

Winning the big one – Champions League 2012

It’s impossible to discuss Chelsea’s penalty shoot-outs without recalling arguably the biggest moment in club history on 19 May 2012.

Given all the heartaches we had suffered in the competition up to that point, it seemed somewhat apt that we were made to suffer once again when we watched Juan Mata miss our opening attempt against Bayern Munich, right in front of their fans at the home stadium.

But what followed will never be forgotten by Blues fans as David Luiz, Lampard and Ashley Cole coolly fired home their efforts while Cech denied Ivica Olic and Bastien Schweinsteiger with a pair of magnificent saves to set the stage for Drogba to seal our first-ever Champions League triumph.