Can Liverpool achieve the quadruple? Reds closer to clean sweep than any other side in history

Jurgen Klopp's men have taken the quadruple chase further than ever before - even if they fail to land any more trophies this season.

The Quadruple. The Holy Grail of English football - never achieved in its long history.

But Liverpool are now closer than any side previously to achieving the feat - one which would eclipse Manchester United's Treble of 1998/99.

Regardless of results, the earliest the Reds' hopes of winning all four trophies can now end is May 11.

Here's our look back at the teams who have come closest to claiming the 'Quadruple' in the past - and what they actually ended up with.

Manchester City (2018/19) - April 17

City's 2018/19 outfit were still in the hunt for every piece of silverware come mid-April but those hopes were destroyed on a remarkable night at the Etihad.

Tottenham arrived holding a 1-0 lead from the first leg of their Champions League quarter-final but any thoughts of them trying to defend that lead were quickly forgotten as five goals were scored in the opening 21 minutes.

An all-time classic duly unfolded, ultimately settled by Fernando Llorente's goal which many felt came off his hand, but the outcome is probably best remembered for VAR cancelling out what had appeared to be an injury-time winner from Raheem Sterling.

With the memories of that contest still vivid, it is often forgotten that City went on to win an unprecedented domestic treble that season.

Having already defeated Chelsea to win the League Cup, they pipped Liverpool to the title by a point and then crushed Watford 6-0 in the FA Cup final.

Not quite a quad squad but still a remarkable team.

Manchester City (2020/21) - April 17

Last season, April 17 again proved to be the day it all went wrong for City's Quadruple bid.

It was the day they lost 1-0 to Chelsea in the FA Cup semi-final, a game of considerably less drama than the Spurs one of 2018/19. Played behind closed doors, it was decided by a goal from Hakim Ziyech.

Chelsea would also beat them 1-0 in the Champions League final - Kai Havertz the man on target this time - but City did have the consolation of regaining the Premier League title (by 12 points) and winning the League Cup by defeating Tottenham 1-0.

Manchester United (2008/09) - April 19

United's most famous team won the Treble of Premier League, Champions League and FA Cup a decade earlier but this was the closest a Sir Alex Ferguson side got to winning the Quadruple.

Such hopes were finally dashed by Everton at Wembley in the FA Cup semi-final - although some would point the finger at referee Mike Riley, who failed to award what looked a stonewall penalty.

A tedious game ended goalless but Everton won the shoot-out 4-2.

Tim Howard Dimitar Berbatov

This match is a nod to the problem Jurgen Klopp will have in the coming weeks as Liverpool chase success on four fronts.

Ferguson rested star men Cristiano Ronaldo, Wayne Rooney and Edwin van der Sar that day and paid the price.

They did finish with the Premier League and League Cup trophies in their cabinet but lost the Champions League final 2-0 to Barcelona.

For the record, the 98/99 Treble team actually lost their Quadruple chance on December 2, losing in the League Cup quarter-finals to eventual winners Tottenham.

Chelsea (2006/07) - May 1

Chelsea are the only previous team to have taken the Quadruple chase into May.

In truth, their Premier League title hopes were already beginning to fade by the time they headed to Anfield for the second leg of their Champions League semi-final with Liverpool.

A 1-0 loss on the night resulted in a penalty shoot-out, one the hosts dominated, winning it 4-1.

Jose Mourinho's side did win both domestic cups that season but were runners-up to Man Utd in the league. Having got within three points of the Red Devils in mid-April, they drew their last five games to finish six points adrift.

The Blues played 63 games in total that season - a number Liverpool will match if they win the Quadruple this term.

Liverpool (2021/22) - TBC

Liverpool are now just six games from history - although things aren't currently in their own hands with Manchester City needing to slip up at some stage if they are to win the Premier League.

Can they do it? Take a look at their fixtures and see what you think...

Sat May 7 - Tottenham H (PL)

Tue May 10 - Aston Villa A (PL)

Sat May 14 - Chelsea N (FAC)

Tue May 17 - Southampton A (PL)

Sun May 22 - Wolves H (PL)

Sat May 28 - Real Madrid N (CL)

READ MORE: Ronaldo's on the hat-trick trail but how does Premier League treble tally compare to past seasons?

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