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

Liverpool beat Chelsea on penalties to win the FA Cup and Carabao Cup; Jurgen Klopp's side are second in the Premier League, one point behind Manchester City, ahead of the final day on Sunday; the Reds have reached the Champions League final and will face Real Madrid on May 28

Jurgen Klopp

Liverpool's quest to win a historic Quadruple remains in tact after they beat Southampton 2-1 on Tuesday night to ensure the Premier League title race will go down to the final day.

Goals from Takumi Minamino and Joel Matip cancelled out Nathan Redmond's opener and mean Liverpool will go into the final round of fixtures just one point behind leaders Manchester City.

If Pep Guardiola's side fail to beat Aston Villa at the Etihad on Sunday it will open the door for Liverpool, who could win the title if they beat Wolves at home.

Liverpool's win at Southampton was their first game since they secured their second trophy of the season by beating Chelsea in the FA Cup final on Saturday, meaning Jurgen Klopp's side have now gone further into a season than any other English side before them.

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FREE TO WATCH: Highlights from Liverpool’s win against Southampton in the Premier League

Liverpool once again beat the Blues on penalties at Wembley, having secured their first trophy of the season with an 11-10 shootout win in the Carabao Cup final in February against the same opponents.

Saturday's FA Cup final was an enthralling goalless draw that ended in another shootout, with Kostas Tsimikas scoring the winning spot kick as Liverpool won 6-5 on penalties.

Liverpool have surpassed the Chelsea side of 2006/07, whose own Quadruple challenge lasted all the way until May 1 of that campaign before losing to Liverpool in the Champions League semi-finals.

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Liverpool lift the FA Cup trophy after beating Chelsea on penalties
Image: Liverpool lift the FA Cup trophy after beating Chelsea on penalties

In total, Liverpool face a gruelling seven-match schedule in May, having also reached the Champions League final on May 28, when they face Real Madrid in a repeat of the 2018 showpiece event.

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?

The English Quad?

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

Prior to this season, the closest any top-flight side had ever got to winning all four major trophies in a single campaign was Chelsea back in 2006/07.

Heading into May of that season, 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 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.

Manchester United 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 and the latter after a defeat to Chelsea in the FA Cup semi-finals.

Liverpool's current quest, though, will now last at least the Premier League's final round of fixtures on Sunday, meaning their Quadruple campaign will have lasted longer than any other English team's in history.

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
Liverpool (2021-22) Won Won Second Final vs Real Madrid Will last till at least May 22
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

Past Reds efforts

You would have thought Liverpool have come close before, but actually they have not, despite winning the League Cup four years in a row from 1981.

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 Won Currently second Final vs Real Madrid Will last till at least May 22
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

Celtic Inter Milan 1967 European Cup final Lisbon Lions
Image: Jock Stein's Celtic won the Quadruple in 1966-67

In the first season in England when four trophies were up for grabs in 1960/61, it was Burnley who came closest 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 European Cup won by a British team after victory over Inter Milan.

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

Thomas Tuchel embraces Neymar after the game
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 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:

May 22 - Wolves (H) Premier League

May 28 - Real Madrid (N) Champions League final

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