Arsenal and Man City are chasing the quadruple – how close did Ferguson, Mourinho, Klopp get?

No English team has ever won the quadruple.

Winning the domestic league championship, European Cup/Champions League, FA Cup and League Cup has so far proven to be an insurmountable task, but this season represents an opportunity for Arsenal and Manchester City to see whether they can create history.

Currently first and second in the Premier League table (though Arsenal are seven points ahead, they have played one top-flight game more and must still visit City’s Etihad Stadium, where they have not won since January 2015, next month) and into the last 16 of the Champions League, the two teams meet in the Carabao-sponsored League Cup final on March 22.

Providing they both advance into the FA Cup quarter-finals from their last-16 ties against Mansfield Town and Newcastle United this weekend and also see off Bayer Leverkusen and Real Madrid respectively in Europe over the next couple of midweeks, victory that Sunday at Wembley will give one of them the chance to kick on in their quest for footballing immortality.

Pep Guardiola’s City have come close to the quadruple in the recent past, winning the Premier League, FA Cup and Champions League in 2022-23, but they had been knocked out of the Carabao Cup in the quarter-finals by a Southampton side who ended up not just relegated but bottom of the top flight. Before then, Manchester United completed that same treble but had also lost in the last eight of the League Cup, to Tottenham Hotspur.

With the important caveat of winning the League Cup — which is often seen as the least prestigious of the four trophies involved — first, Chelsea nearly managed it in 2006-07, at a time when Jose Mourinho, then their manager, was in his pomp. They lifted the FA Cup too, but fell painfully short in Europe and in the Premier League (more on that shortly).

The two Manchester clubs and Liverpool have also been within sniffing distance of claiming the other three trophies after lifting the League Cup, only to then miss out in one or more of those other competitions.

If Arsenal or City are to create history over the next three months, it will require perfection… and undoubtedly an element of good fortune along the way.

Arsenal manager Mikel Arteta, left, and Manchester City counterpart Pep Guardiola will go head-to-head in the Carabao Cup final this month (Michael Regan/Getty Images)

In that 2006-07 season, Chelsea kick-started their quadruple hopes by beating Arsenal 2-1 in the League Cup final.

Despite winning that final, they still had plenty of work to do on the Premier League run-in, and were trailing Manchester United by nine points on the February day they celebrated that League Cup success, albeit with a game in hand over Sir Alex Ferguson’s side.

Although Mourinho’s Chelsea continued to progress in the FA Cup, which they eventually won by beating United in the final in late May, they had already been knocked out of the Champions League, losing to Liverpool over two semi-final legs a couple of weeks earlier. They also failed to close the gap to United at the top of the table, who ended the campaign six points ahead of them.

It was United’s turn in 2008-09, having won a Premier League and Champions League double in 2007-08, to lift the League Cup in February and still be active with a chance of defending their Premier League and Champions League crowns while also securing the FA Cup. That squad included a front three of Cristiano Ronaldo, Carlos Tevez and Wayne Rooney, with Rio Ferdinand and Nemanja Vidic in the heart of defence.

“With United, we established a mentality around that particular squad that was built throughout the years before,” Rene Meulensteen, an assistant coach under Ferguson at the time, tells The Athletic. “It was a certainty that we were going to win trophies; nobody doubted that. That was our mentality.”

For Ferguson, Meulensteen added, winning the Premier League was always the “main focus”, but explained how lifting the League Cup — traditionally the first trophy on offer each season — “reinforced what we stood for and what we wanted to achieve”.

“It just creates a good-feel factor,” the 61-year-old says.

Meulensteen with Ferguson in 2009 (Paul Ellis/AFP via Getty Images)

But even that great United team of the late 2000s were unable to buck the quadruple trend, retaining the title but succumbing to Everton in an FA Cup semi-final that went to a penalty shootout and losing to a fabulous Barcelona team in the Champions League final.

“You need to look at the opposition that you’re facing, and we faced obviously a very, very strong Barcelona at the time in the Champions League final, and we lost to Everton on penalties in the FA Cup, but we should have had a penalty with Danny Welbeck,” Meulensteen says of those two pivotal fixtures.

“What makes it (winning the quadruple) so difficult is that because you are going so deep in every single tournament, you do need to start resting important players. That is how Sir Alex managed the squad during that particular time.

“All the players, when it comes to those games, want to play, but the manager has to make those tough decisions at times.”

Manuel Pellegrini’s 2013-14 Manchester City squad won the League Cup and Premier League but fell short in the FA Cup (quarter-finals vs Wigan Athletic) and Champions League (round of 16 vs Barcelona), before the club hired Guardiola ahead of the 2016-17 season.

Guardiola has shown himself capable of managing a team to a historic trophy haul, winning six titles in 2008-09, culminating in beating Manchester United in that Champions League final. His Barcelona team also won La Liga, the Copa del Rey, Spain’s Super Cup, the UEFA Super Cup and the old version of FIFA’s Club World Cup that season, so if anyone knows how to get over the line in multiple competitions, it is the 55-year-old.

However, City have had chances to complete the quadruple by firstly winning the League Cup three seasons in a row under the Catalan (2018-19, 2019-20, 2020-2021), but found themselves coming up short in one of the other three competitions.

During that 2018-19 campaign, Guardiola, in quotes reported by the BBCsaid it would be “almost impossible” to achieve the four-trophy feat.

“Surviving is a miracle,” Guardiola said after his team beat Brighton & Hove Albion in the FA Cup semi-finals. “Nobody has done it (won the quadruple), so why can we do it?

“It is almost impossible to achieve everything — that is the truth.”

For Meulensteen, managing your squad when it comes to the business end of the season is crucial if a team are to win a quadruple. He noted how Ferguson would often think “three games ahead” in terms of team selection, working out when the most appropriate time was to rest certain players.

This, though, should be viewed as a blessing.

“At the end of the day, you want to be there,” Meulensteen said. “As Manchester United, we wanted to have a lot of games in April and May, because that’s where the prizes are being given.

“Nowadays, if you do go far in the Champions League and in the FA Cup, you are going to have to play a lot in the final weeks, which is going to be a Sunday-Wednesday or Saturday-Tuesday situation. And you have to play those games anyway, so they might as well be big games where you have something to play for, and your big players thrive on that.”

It was Liverpool’s turn to win the Carabao Cup in 2021-22, and they came agonisingly close to lifting the other three trophies too with Jurgen Klopp in charge.

That April, they were one point behind City on the Premier League run-in, and had made it into the Champions League semi-finals and FA Cup final.

“We love being in this situation. It’s incredibly tough — we play pretty much all the time,” said manager Klopp, in quotes reported by TNT Sports. “You cannot plan that you are still in everything.

“But we know there’s nothing we have achieved so far, or not a lot. We won one competition, that’s great, but there are three others to go.”

Klopp said he loved his Liverpool side going for four trophies (Clive Brunskill/Getty Images)

They fell agonisingly short, beating Chelsea in the FA Cup final but then finishing a point behind City and losing to Real Madrid in the Champions League final.

Two years later, during what proved Klopp’s final season in charge, Liverpool were still active in four competitions during the second half of the campaign, albeit playing in the second-tier Europa League as opposed to the Champions League.

They again won the Carabao Cup, but finished third in the Premier League, having been knocked out of both the FA Cup and Europe in the quarter-finals.

There is a reason no club has yet managed to win the quadruple; history has shown it is almost impossible, as Guardiola suggested six years ago.

But Arsenal and City currently still have the chance to do it this season — and time will soon tell which of the two clubs are going to continue to be in with a shot after their Wembley showdown.