Liverpool’s Quadruple quest: How do Jurgen Klopp’s side fare in historic bid?

Liverpool’s historic quest for a Quadruple continues when they host Watford in the Premier League on Saturday lunchtime, but how have other sides fared in their own bids to win all four major trophies in a single season?

Liverpool are still in with a chance of an unprecedented Quadruple this campaign, as unlikely as that sounds, as we enter the final stretch of the season.

It is ‘squeaky-bum time,’ as Sir Alex Ferguson would say, with Jurgen Klopp’s side now just a point behind leaders Man City as we enter the final nine games of the season after an impressive nine-game winning run in the league saw the champions’ seemingly unsurmountable 14-point lead on January 15 evaporate away.

Manchester City

Sunday 10th April 4:00pm Kick off 4:30pm

Meanwhile, Liverpool also take on Benfica in the Champions League quarter-finals, the first leg of which is in Lisbon on Tuesday night, before an FA Cup semi-final clash with rivals City at Wembley on April 16.

In total, Liverpool could face a gruelling nine-match schedule in April – including a potential title decider at City live on Sky Sports on April 10 – were they to continue their bid for the Quadruple and progress to the semi-finals of the Champions League, followed by another seven games in May if they also make it through to the finals of both the FA and European Cups.

Neville: Liverpool can do something special

Speaking during the latest edition of The Overlap’s live fan debate, Sky SportsGary Neville said he was concerned Liverpool could do ‘something special’ in the run-in to the season.

“They’re going to do something dangerous this season and it’s scary as a Man United fan to say that,” said Neville.

“I really do worry that they will go on and win three or four trophies, it would concern me. I think they are unbelievably dangerous, and I think they’re going to do something pretty special this season.

“When I watched them against Arsenal, there is nothing I saw that didn’t tell me they’re going to go and win the title. That is a title-winning performance.

“I think Liverpool will win the league. They’re dangerous in the other two competitions and I think they’ll do something special because of those five strikers they’ve got.”

So, how have other English teams got on when faced with such a daunting challenge, while surely the trophy-laden Liverpool sides of the 80s must have gone close to achieving the feat? And what about some of the great European giants of years gone by?

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The English Quad?

As is surely common knowledge by now, no English team has ever won the Quadruple.

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The closest any top-flight side has ever got to winning all four major trophies in a single season was Chelsea in the 2006-07 campaign.

Heading into May 2007, Jose Mourinho’s back-to-back Premier League champions had already landed the League Cup after beating Arsenal 2-1 at the Millennium Stadium, while they had an FA Cup final date to look forward to with Manchester United, who they were also going toe to toe with in the league.

However, the Blues’ challenge ended when they lost 4-1 on penalties to Liverpool at Anfield in the second leg of their Champions League semi-final, while they would also go on to lose their title to United.

Image: Rafa Benitez and his Chelsea counterpart Jose Mourinho (right) on the touchline at Anfield as the Blues' Quadruple dreams ended in the second leg of the 2007 Champions League semi-final

Speaking of United, they also came close to making history in 2008-09, only to slip up in the semi-finals of the FA Cup when losing 4-2 on penalties to Everton, although they did then get beaten 2-0 by Barcelona in that season’s Champions League final in Rome.

And, of course, Pep Guardiola’s City side have had numerous Quadruple bids as well since the Catalan arrived at the Etihad, the closest being in 2018-19 and last season. However, the former challenge was ended by Tottenham in the Champions League last eight, while the latter after a defeat to Chelsea in the FA Cup semi-finals.

Liverpool’s current quest, though, will last to at least April 13 when their Champions League last-eight clash against Benfica concludes with the second leg at Anfield.

And before you ask, United’s famous Treble-winning season of 1998-99 actually included a League Cup quarter-final loss at Spurs in the December of that campaign.

English Quadruple attempts

League Cup FA Cup League Champions League Bid ended
Chelsea (2006-07) Won Won Second Semi-finals May 1
Man Utd (2008-09) Won Semi-finals Won Runners-up April 19
Man City (2018-19) Won Won Won Quarter-finals April 17
Man City (2020-21) Won Semi-finals Won Runners-up April 17
Liverpool (2021-22) Won Semi-final vs City Currently second Quarter-final vs Benfica Wil last till at least April 13
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Past Reds efforts

Well, you would have thought so, but actually they did not, despite winning the League Cup four years in a row from 1981.

However, it was the FA Cup that ultimately proved to be Liverpool’s Achilles’ heel in each of those four campaigns, with the Reds never managing to make it past the fifth round, meaning the closest they came was in 1982-83, only for a shock 2-1 home defeat to second division Brighton to end their Quadruple dreams in February.

And it was Brighton again in the cup who scuppered the Reds’ chances of winning all four trophies in their Treble-winning campaign the following season.

Liverpool’s Quadruple attempts

League Cup FA Cup League European Cup Bid ended
1982-83 Won Fifth round Won Quarter-finals Feb 20
1981-82 Won Fifth round Won Quarter-finals Feb 13
1983-84 Won Fourth round Won Won Jan 29
1980-81 Won Fourth round Fifth Won Jan 24

Klopp’s quests

Oddly enough, despite Klopp’s ‘Mentality Monsters’ barely losing a game between 2018 and 2020, they never actually came close to winning the Quadruple.

In fact, the nearest they came to achieving the feat was in their title-winning campaign of 2019-20, only for a youth side – selected because of a fixture clash with the Club World Cup – to lose 5-0 at Aston Villa in the League Cup quarter-finals to put an end that dream.

Klopp’s Liverpool Quadruple attempts

League Cup FA Cup League Champions League Bid ended
2021-22 Won Semi-final vs City Currently second Quarter-final vs Benfica Wil last till at least April 13
2019-20 Quarter-final Fifth round Won Last 16 Dec 17
2020-21 Fourth round Fourth round Third Quarter-final Oct 1
2018-19 Third round Third round Second Winners Sept 26
2017-18 Third round Fourth round Fourth Runners-up Sept 19

The British bids

Image: Jock Stein's Celtic won the Quadruple in 1966-67

Well Burnley did in 1960-61, the first season in England when four trophies were up for grabs, before losing to Hamburg in the last eight of the European Cup in March 1961.

However, Celtic did manage to accomplish the seemingly impossible in 1966-67 when Jock Stein’s ‘Lisbon Lions’ won it all – the Scottish First Division, League Cup and Scottish Cup, followed by the first-ever European Cup won by a British team after victory over Inter Milan.

Image: Delighted Celtic players show off the 1967 European Cup to their fans

Continental challenge

Well, the first thing to point out here is that up until the 2019-20 season, France, as in England, was the only other country in Europe’s top-five major leagues to have an extra cup competition in the form of the League Cup, or Coupe de la Ligue.

So that explains why European giants like Real Madrid, Barcelona, Bayern Munich and Juventus have all never previously won the Quadruple.

Paris Saint-Germain did, though, recently come within a whisker of pulling it off under Thomas Tuchel, only to fall agonisingly at the final hurdle.

Image: PSG's Quadruple bid came to an end at the final hurdle after defeat to Bayern in the 2019-20 Champions League final

The big-spending Parisians were awarded that season’s Ligue 1 title in April based on a points-per-game ratio after the campaign was prematurely curtailed due to the COVID-19 pandemic.

However, when the season did eventually resume, PSG beat St Etienne 1-0 in the Coupe de France final on July 24, before edging out Lyon 6-5 on penalties to claim the Coupe de la Ligue the following weekend.

Then, when the Champions League also returned in August, Tuchel’s team made it all the way to the final for the first time in the club’s history, before unluckily losing 1-0 to Bayern Munich in Lisbon.

All of which shows just what a mountain Klopp and Co still face in order to make history this season…

Liverpool’s fixture schedule:

To be rearranged: Aston Villa (a) Premier League, live on Sky Sports

April 2 – Watford (H) Premier League

April 5 – Benfica (a) Champions League QF first leg

April 10 – Man City (a) Premier League, live on Sky Sports

April 13 – Benfica (H) Champions League QF second leg

April 16 – Man City (Wembley) FA Cup semi-final

April 19 – Man United (H) Premier League, live on Sky Sports

April 24 – Everton (H) Premier League, live on Sky Sports

April 26/27 – Villarreal/Bayern Munich Champions League SF first leg *

April 30 – Newcastle (a) Premier League

May 3/4 – Villarreal/Bayern Munich Champions League SF second leg *

May 7 – Tottenham (H) Premier League

May 14 – FA Cup final*

May 15 – Southampton (a) Premier League

May 22 – Wolves (H) Premier League

May 28 – Champions League final *

* Subject to progress

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