It is all to play for at the midway point of our Carabao Cup semi-final against Tottenham, and here we look back on our record in the 26 previous two-legged last-four cup ties we have contested to check for any notes or anomalies of historical interest.
Tuesday night’s narrow defeat at Wembley was the second occasion we have lost the first leg of a semi-final 1-0. The other? Vicenza away in 1998, which we sensationally overturned at the Bridge to advance to the Cup Winners’ Cup final in Stockholm.
That success is one of two semi-final ties which we have reversed after losing the first leg. The other was earlier in the very same season, against Arsenal in the League Cup, when we lost 2-1 at Highbury before winning 3-1 at home in Gianluca Vialli’s first match in charge.
We have twice won the first leg but not advanced, against Tottenham in 2002 in the League Cup, and Liverpool in 2007 in the Champions League. Drawing first and then losing the second leg is a much more frequent occurrence. That has happened five times, including at the same stage of the Carabao Cup last season.
Our overall record in two-legged semi-final ties is: played 26, won 12, lost 14. We have progressed in exactly 50 per cent (seven of 14) since Roman Abramovich bought the club.
Here is the full list and a brief line on what happened in each, starting way back in 1965…
1964/65 - Aston Villa - League Cup
We won 3-2 at Villa Park in the first leg, Bobby Tambling among the scorers, before George Graham’s goal earned us a 1-1 draw back at the Bridge for us to advance to our maiden League Cup final with a 4-3 aggregate victory.
1965/66 - Barcelona - Inter-Cities Fairs Cup
We matched Barca’s 2-0 victory at the Nou Camp with a 2-0 victory of our own at the Bridge. A semi-final play-off was required, a toss of the coin meant it was played in Spain, and we lost 5-0 at the end of a long season.
1970/71 - Manchester City - Cup Winners’ Cup
1-0 victories in both legs make this one of two semi-final ties we have won both legs of.
1971/72 - Tottenham - League Cup
We beat Spurs 3-2 at the Bridge before Christmas in 1971, and in the return leg an Alan Hudson equaliser at White Hart Lane secured us a 2-2 draw and a 5-4 aggregate victory.
1972/73 – Norwich City – League Cup
Starting a run of last-four losses, Norwich defeated us 2-0 and 1-0 to advance to Wembley without a hitch.
1984/85 – Sunderland – League Cup
A 2-0 loss at an icy Roker Park left us with a mountain to climb and it proved insurmountable as we went down 3-2 on a troubled night at the Bridge, despite taking the lead.
1990/91 – Sheffield Wednesday - League Cup
Another pair of very disappointing losses in the League Cup, this time by 2-0 and 3-1 scorelines against a Sheffield Wednesday side from a division below.
1994/95 – Real Zaragoza – Cup Winners’ Cup
After a 3-0 defeat in northern Spain, a Paul Furlong goal briefly gave us hope of a comeback but it was cancelled out and the final 3-1 margin of victory was not quite enough.
1997/98 – Arsenal – League Cup
At 2-0 down in the first leg against the soon-to-be-crowned Double winners, things were not looking good. But Mark Hughes got a goal back and when the teams reconvened at Stamford Bridge, the Blues produced a performance for the ages with Hughes, Roberto Di Matteo and Dan Petrescu netting. A late Dennis Bergkamp penalty proved a mere consolation as Chelsea made it to Wembley with a 4-3 aggregate success.
1997/98 – Vicenza – Cup Winners’ Cup
A couple of months later we were at it again! Having lost 1-0 in Italy and then gone 1-0 down on the night at the Bridge, the chances of making it to a second European final seemed unlikely, but we roared back and completed an amazing comeback to win 3-1 on the night and 3-2 on aggregate.
1998/99 – Mallorca – Cup Winners’ Cup
A 1-1 draw at Stamford Bridge was followed by a 1-0 loss in Mallorca, ending hopes of retaining the Cup Winners’ Cup.
2001/02 – Tottenham – League Cup
Easily the most emphatic reversal in fortunes in our two-legged semi-final history. We beat Spurs 2-1 at Stamford Bridge but collapsed in the second leg in north London, losing 5-1.
2003/04 – Monaco – Champions League
The Blues couldn’t capitalise against the 10 men of Monaco, eventually losing 3-1, and even though we were going through on away goals at 2-0 up back at the Bridge, the Principality side hit back to draw 2-2.
2004/05 – Manchester United – League Cup
We advanced to our first final under Jose Mourinho with a 2-1 second-leg victory at Old Trafford, Damien Duff scoring a late winner following a goalless opener in west London.
2004/05 – Liverpool – Champions League
Another first-leg stalemate was followed by a night of drama in Merseyside and a solitary goal that is still disputed to this day.
2006/07 – Wycombe Wanderers – League Cup
A 1-1 draw at Adams Park wasn’t the result most expected, but we made light work of the third-tier Chairboys in the second leg, winning 4-0 back on home soil.
2006/07 – Liverpool – Champions League
Penalties were required to separate the sides after another predictably close semi-final tie between now-regular rivals. Both sides won their home leg 1-0, and it was Liverpool who held their nerves from 12 yards at Anfield.
2007/08 – Everton – League Cup
A last-gasp own goal meant we took an advantage to Goodison Park, where a 1-0 win completed the job.
2007/08 – Liverpool – Champions League
Familiar opposition at a familiar stage, but this time a different outcome! After a 1-1 draw at Anfield, when we equalised with virtually the last kick – well, header – of the game, we dramatically overcame Liverpool back at the Bridge, 3-2 after extra-time, and so 4-3 on aggregate.
2008/09 – Barcelona – Champions League
A heartbreaking stoppage-time leveller from Andres Iniesta took Barca through on away goals after a 0-0 in Catalonia.
2011/12 – Barcelona – Champions League
Against all the odds we made it to a second Champions League final, simultaneously avenging previous Barcelona demons. After a tense 1-0 win at the Bridge, we somehow came back from 2-0 down with 10 men to make it to Munich.
2012/13 – Swansea – League Cup
The damage was done in the first leg with two Michu goals for the Swans, and the goalless draw that followed in South Wales was not enough.
2012/13 – Basel – Europa League
Two victories and few scares for the Blues en route to Amsterdam, with a 2-1 victory in Switzerland backed up by a 3-1 success at the Bridge.
2013/14 – Atletico Madrid – Champions League
The goalless draw we fought to earn in the Spanish capital was a good start to the tie, but Atletico’s class told in the second leg as they won 3-1 with Diego Costa among their scorers.
2014/15 – Liverpool – League Cup
We were going through on away goals after a 1-1 draw at Anfield, but Branislav Ivanovic’s extra-time header in SW6 made sure securing a 2-1 aggregate success.
2017/18 – Arsenal – League Cup
We went ahead in the tie early in the second leg after a goalless opener, but Arsenal fought back at the Emirates to win 2-1 on the night and on aggregate.