Arsenal sixth as deepest Quadruple runs ever ranked, with sweary Guardiola in sight | OneFootball

Arsenal are heading into the final weeks of a season with the Quadruple still possible, but they have a way to go to beat a Liverpool record.

Manchester City, Manchester United and Chelsea have all also gone deeper into a campaign before stumbling in either the Premier League, Champions League, FA Cup or League Cup.

Arsenal are top of the Premier League, in the Champions League and FA Cup quarter-finals and the League Cup final; this is the sixth-latest date in a season that a Premier League side could still win the Quadruple.

The Gunners have plenty of work to do to catch the other five.

5) Manchester City, 2018/19 – April 17

Pep Guardiola had previously described the prospect of a Manchester City Quadruple as “fantasy”, greeting the first question he fielded about it as manager at the Etihad with a wonderfully exasperated “what the f**k” in September 2016.

It was a daft concept back then, but even when Manchester City reached the FA Cup final as Premier League leaders, League Cup winners and Champions League quarter-finalists in 2019, Guardiola deemed it “almost impossible” to spin all four plates simultaneously.

He celebrated a “‘little’ Quadruple” when channelling his inner Mourinho by chucking the Community Shield in with a domestic Treble once deemed “impossible” by Sir Alex Ferguson.

But any hope of success across the board was dashed by Fernando Llorente’s hip and away goals in a pre-VAR world.

4) Manchester City, 2020/21 – April 17

Three years later, Manchester City found themselves at a similar crossroads behind closed doors: runaway Premier League leaders in the League Cup final and semi-final stage of both the Champions League and FA Cup.

Yet still – inevitably and understandably – Guardiola refused to feed into the notion that winning all four competitions was achievable.

Even when his players expressed their belief it could be done, the manager shot it down. “I am older than Mr Zinchenko,” he said, responding to the Ukrainian’s claim about the squad’s “hungry eyes”: “I have more experience and I am not agreeing with him.”

Guardiola was proved right soon enough – on exactly the same day as three seasons before. Chelsea tripped them up in the FA Cup semi-final a month before ending their European dream too.

3) Manchester United, 2008/09 – April 19

“We could go to Fulham in the FA Cup, the ball comes off someone’s backside and we are out of that one,” said a dismissive Ferguson when asked about the Quintuple, Manchester United having already won the Club World Cup back in December.

It could actually have been a Sextuple – the Community Shield had been retained in August – but entirely non-existent Septuple chat was sadly rendered moot with defeat to Zenit St Petersburg in the UEFA Super Cup final.

Manchester United recovered from that eternal shame to lead the Premier League table by a point with a game in hand over Liverpool by late April, having beaten Spurs in the League Cup final and reached the Champions League semis, where Arsenal lay in wait.

And Fulham were navigated in the FA Cup quarter-final without any backside-based ricochet shenanigans in the most routine of 4-0 wins. But a similar level of opponent in Everton did prove their undoing in the semis.

With Cristiano Ronaldo and Michael Carrick among those rested while Wayne Rooney succumbed to injury, Manchester United were held to a goalless draw and then beaten on penalties by David Moyes’ side.

Barcelona sorted them out in the Champions League final anyway, despite the usual Guardiola head-patting.

Manchester United did hold on in the Premier League to finish off a Quadruple which is weirdly not celebrated as much as their poxy Treble a decade earlier.

2) Chelsea, 2006/07 – May 1

Jose Mourinho went entirely against the grain as Chelsea approached the home straight in 2007.

“My boys have been brilliant and the quadruple is possible,” he said, eschewing the boring realism and practicality reserved for nerds like Ferguson and Guardiola to indulge in some creative thinking.

Chelsea, at that stage, were six points back from Manchester United with eight games to play in the Premier League, while preparing for a Champions League quarter-final with Valencia and FA Cup semi-final against Blackburn.

Didier Drogba had obviously already handled Arsenal in the League Cup final.

The brilliant big-game player did the same against Manchester United in the FA Cup final but Chelsea could not catch Ferguson’s men in the league. By then, the Quadruple had gone up in smoke anyway at the hands of a painfully familiar foe.

Jorge Valdano saw ‘sh*t hanging from a stick’; the rest of us witnessed Rafael Benitez’s Liverpool thwart Chelsea in another Champions League semi-final, this time on penalties as the season entered its final month.

1) Liverpool, 2021/22 – May 22

It will take an ungodly effort to kick the Quadruple can as far down the road as Liverpool in 2022. Jurgen Klopp’s side played the maximum number of games and took it all down to the wire, emerging with some but not all of the requisite silverware.

Chelsea were beaten on penalties in both domestic finals. Another Premier League title race with Manchester City went down to the wire. Real Madrid were waiting in the Champions League final.

As late as the 75th minute of the Premier League’s final day, a clean Liverpool sweep felt written. Manchester City were losing 2-0 at home to Aston Villa and Liverpool, while still level with Wolves at Anfield, were knocking relentlessly on that door.

Both sides emerged victorious and thus Manchester City pipped their rivals at the 90-plus-point post. Then Thibaut Courtois selfishly scuppered the European leg