Penalty shoot-outs
From TheChels.info - The Chelsea Football Club Wiki
Below is Chelsea's full record in penalty shoot-outs. First introduced in football during the 1970s, Chelsea have taken part in 21 competitive shoot-outs, winning nine and losing twelve.
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Shoot-outs involving Chelsea
Competitive
| Season | Day | D | M | Year | Comp | Opposition | Venue | Result | Score | Notes |
| 1983-84 | Tue | 25 | Oct | 1983 | LC | Leicester City | Home | Won | 4-3 | |
| 1985-86 | Wed | 13 | Nov | 1985 | FMC | West Bromwich Albion | Away | Won | 5-4 | |
| 1990-91 | Mon | 18 | Feb | 1991 | FMC | Luton Town | Home | Lost | 1-4 | |
| 1991-92 | Tue | 26 | Nov | 1991 | FMC | Ipswich Town | Home | Won | 4-3 | |
| 1994-95 | Wed | 8 | Feb | 1995 | FAC | Millwall | Home | Lost | 4-5 | |
| 1995-96 | Wed | 17 | Jan | 1996 | FAC | Newcastle United | Away | Won | 4-2 | |
| 1997-98 | Sun | 3 | Aug | 1997 | CS | Manchester United | Neutral* | Lost | 2-4 | *Wembley |
| 1997-98 | Wed | 15 | Oct | 1997 | LC | Blackburn Rovers | Home | Won | 4-1 | |
| 1997-98 | Wed | 7 | Jan | 1998 | LC | Ipswich Town | Away | Won | 4-1 | |
| 2005-06 | Wed | 26 | Oct | 2005 | LC | Charlton Athletic | Home | Lost | 4-5 | |
| 2006-07 | Tue | 1 | May | 2007 | UCL | Liverpool | Away | Lost | 1-4 | |
| 2007-08 | Sun | 5 | Aug | 2007 | CS | Manchester United | Neutral* | Lost | 0-3 | *Wembley |
| 2007-08 | Wed | 21 | May | 2008 | UCL | Manchester United | Neutral* | Lost | 5-6 | *Luzhniki Stadium, Moscow |
| 2008-09 | Wed | 12 | Nov | 2008 | LC | Burnley | Home | Lost | 4-5 | |
| 2009-10 | Sun | 9 | Aug | 2009 | CS | Manchester United | Neutral* | Won | 4-1 | *Wembley |
| 2009-10 | Wed | 2 | Dec | 2009 | LC | Blackburn Rovers | Away | Lost | 3-4 | |
| 2010-11 | Sat | 18 | Feb | 2011 | FAC | Everton | Home | Lost | 3-4 | |
| 2011-12 | Wed | 21 | Sep | 2011 | LC | Fulham | Home | Won | 4-3 | |
| 2011-12 | Sat | 19 | May | 2012 | UCL | Bayern Munich | Neutral* | Won | 4-3 | *Allianz Arena, Munich |
| 2013-14 | Fri | 30 | Aug | 2013 | ESC | Bayern Munich | Neutral* | Lost | 4-5 | *Eden Arena, Prague |
| 2015-16 | Tue | 27 | Oct | 2015 | LC | Stoke City | Away | Lost | 4-5 |
Non-competitive
| Day | D | M | Year | Comp | Opposition | Venue | Result | Score | Notes |
| Sat | 31 | July | 1993 | MIT | Ajax | Away* | Won | 4-2 | *Tournament played at White Hart Lane |
| Sat | 13 | Aug | 1994 | Friendly | Valencia | Away | Won | 4-2 | |
| Tue | 3 | Aug | 1996 | UIT | Nottingham Forest | Away | Won | 4-3 | |
| Sat | 26 | Jul | 1997 | UIT | Newcastle United | Away* | Won | 3-1 | *Tournament played at Goodison Park |
| Sun | 27 | Jul | 2003 | PLAC | Newcastle United | Neutral* | Won | 5-4 | *National Stadium, Malaysia |
| Fri | 1 | Aug | 2008 | RRC | Lokomotiv Moscow | Away | Lost | 4-5 | |
| Sat | 25 | July | 2015 | ICC | Paris Saint-Germain | Neutral* | Won | 6-5 | *Bank of America Stadium, Charlotte, NC, USA |
| Tue | 28 | July | 2015 | ICC | Barcelona | Neutral* | Won | 4-2 | *FedEx Field, Maryland |
Penalty takers
Competitive matches only
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