Where Quadruples went horribly wrong: Man Utd join Spurs, Wigan and Nathan Jones in ruining history

Dave Tickner
Liverpool players Virgil van Dijk and Darwin Nunez, Manchester City manager Pep Guardiola with Southampton coach Nathan Jones, and Arsenal striker Thierry Henry
Another Quad bites the dust

Liverpool will embarrassingly fail to win four trophies this season, but at least their tilt at history did not come unstuck against Wigan or Nathan Jones.

Defeat to Manchester United in the FA Cup has ended any hopes of Liverpool winning a Quadruple – and rival fans dismissing it as such because it lacked the necessary taste of Gazprom.

Yet another season has thus passed without a Premier League side winning the lot, but losing a quarter-final in extra-time to Manchester United at Old Trafford is one of the least shameful ways to do it.

Here is precisely where other Quadruple bids went horribly wrong.


Manchester United, 1998/99
Premier League: Won
FA Cup: Won
Champions League: Won
League Cup: Quarter-finals

A philosophical question for you: if a Quadruple bid ends before anyone even actually realises it’s started, does it make a sound? Clearly, nobody was talking about a Quadruple – or even a Treble for that matter – when Manchester United travelled to White Hart Lane in December 1998 for a League Cup quarter-final against Spurs. They were third in the league, five points behind leaders Aston Villa, hadn’t started their FA Cup campaign and were not yet certain of qualification from a Champions League Group of Death alongside Bayern Munich and Barcelona.

But given everything that happened across the rest of that season, and while acknowledging that the Butterfly Effect applies to quickfire Chris Armstrong doubles after half-time every bit as much as it does to the flapping wings of world-destroying insects, you could make a decent case that this is actually the closest anyone has ever come and they didn’t even know it.

Sure, maybe the distraction of a two-legged semi-final against Wimbledon and a final against Leicester might have derailed United’s loftier ambitions but also, probably not. And given that even a phenomenally mediocre Spurs team managed to negotiate those games and actually win themselves a trophy (arguably a more notable thing than United’s Treble) you’d have to imagine an all-conquering United would also have done so; they didn’t lose a single game from December 19 onwards in that fabled campaign.

Essentially it boils down to this: all else being equal, United only needed to see off teams who finished the season 11th, 16th and 10th to add a final (but also first) coat of shiny gloss to their greatest ever season. But David Ginola yet again had other ideas.


Arsenal, 2003/04
Premier League: Won
FA Cup: Semi-finals
Champions League: Quarter-finals
League Cup: Semi-finals

Bit harsh maybe to sully an unbeaten Premier League season with ‘What if?’ chatter, but Arsenal really were a few moments here and there away from something even more spectacular. If you take an unbeaten league season as the baseline, then ending up with only one trophy isn’t great is it? You know, relatively speaking.

All three cups were distinctly winnable as well. Middlesbrough were Arsenal’s destroyers back then, beating the so-called ‘Invincibles’ home and away in the League Cup semi-final and then going on to defeat Bolton at the Millennium Stadium. Arsenal should definitely have won that one, really.

Old rivals Manchester United knocked Arsenal out at the same stage of the FA Cup, but it was the Champions League – the one trophy that continues to elude an Arsenal side handed a difficult route to Wembley glory after finally reaching a quarter-final – that was perhaps the real near-miss. Wayne Bridge’s 87th-minute goal secured victory for Chelsea at Highbury in a wide-open tournament that ended with Jose Mourinho and Porto beating Monaco in the final.

So, in summary: Arsenal’s Invincibles are massive, massive frauds who lost four games to Premier League opponents. Next.


Chelsea, 2006/07
Premier League: 2nd
FA Cup: Winners
Champions League: Semi-finals
League Cup: Winners

In terms of keeping the dream alive as long as possible, few QUAD TILTS can match Chelsea’s 2006/07 effort even if they ultimately missed out on the two biggest gongs.

Jose Mourinho’s teak-tough bastards got all the way to May with the Quad still very much on having pocketed the League Cup and reached the FA Cup final – which they would also go on to win – while battling with Manchester United for the league title. Liverpool awaited in the Champions League semi-final.

Chelsea led 1-0 after the first leg at Stamford Bridge, but Daniel Agger’s goal levelled the tie at Anfield and ultimately sent it to penalties where Arjen Robben and Geremi misses left Liverpool 4-1 winners.

The crestfallen Blues then drew their three remaining Premier League games – making it five league draws in a row – as Manchester United took the title.

Daniel Agger wheels away in celebration after scoring for Liverpool against Chelsea in the 2007 Champions League semi-finals


Manchester United, 2008/09
Premier League: Won
FA Cup: Semi-finals
Champions League: Runner-up
League Cup:

Ten years after being denied by Spurs in their previous quad hunt, United got revenge – it was all anybody could talk about in the build-up – by beating Tottenham on penalties in the League Cup final thanks to some Ben Foster heroics.

It all went tits up in April, though, when United failed to recreate that shoot-out success after another goalless 120 minutes against Everton in the FA Cup semi-final.

United did win eight of their last nine games to secure the Premier League title, including that weird week where Federico Macheda became the most important footballer in the country, but failed to defend their Champions League crown after getting schooled by absolutely peak Barcelona in the final. No shame in that, of course. That defeat to Everton, taking with it the chance of an at-the-time-unprecedented domestic treble, constitutes the real dropped bollock here.


Manchester City, 2013/14
Premier League: Won
FA Cup: Quarter-finals
Champions League: Last 16
League Cup: Won

Not that close really, but still notable for being the first time City’s obvious brilliance prompted chatter around their potential to scoop the lot. Wigan were City’s nemesis at the time, though. Having hilariously and inexplicably denied City in the 2013 FA Cup final, Wigan returned to banter them off a second time.

Sunderland had been dispatched in the League Cup final a week earlier, and City would famously go on to pip slippy Liverpool to the league title with five straight wins at the end of the season. But the quad dream came crashing down a week after the League Cup win as Wigan stunned the Etihad with a 2-1 victory in the FA Cup quarter-final before Barcelona completed the formalities of a last-16 Champions League win with a 2-1 victory at Camp Nou, having won the first leg 2-0 in Manchester.


Manchester City, 2017/18
Premier League: Won
FA Cup: Fifth round
Champions League: Quarter-finals
League Cup: Won

Wigan again. What witchcraft is this? The Latics once again denied the League Cup winners and record-breaking Premier League champions in the FA Cup. Fifth round this time.

The Champions League tilt would come unstuck in a mad tie against domestic opposition miles beneath them in the Premier League table – not for the last time – as Liverpool served notice of the force they were about to become, swatting City aside 3-0 at Anfield before winning 2-1 in the return leg.


Manchester City, 2018/19
Premier League: Won
FA Cup: Won
Champions League: Quarter-finals
League Cup: Won

The second Treble winners to see their Quadruple hopes dashed by Spurs. When’s the parade, yeah? Trophy for that, is there? Hmm?

But unlike United’s 1998/99 bid that only became apparent with the benefit of hindsight, City’s 2018/19 was so dominated by talk of Quadruples that their unprecedented Domestic Treble drew mainly shoulder shrugs and indifference.

The dream died on a gloriously silly night of European football at the Etihad as Spurs arrived with a hard-won 1-0 first-leg lead they gave back almost instantly before Son Heung-min scored two just as quick to take Mauricio Pochettino’s side into an improbable two-goal lead with away-goal buffer to boot, back when such things existed.

City roared back; with barely 20 minutes on the clock the scoreline was an absurd 3-2 to City on the night with Spurs narrowly ahead in the tie by virtue of those away goals.

When Sergio Aguero scored on the hour, City appeared to have done enough only for Fernando Llorente to scramble home a highly controversial third Spurs goal to restore their away-goal advantage. City thought they had won it again in stoppage time only for an agonisingly long VAR check to spot an offside in the build-up.

Reading all that back, it is truly incredible to think that wasn’t even Spurs’ maddest away night of a Champions League run so unutterably bonkers that UEFA had no choice but to scrap the away goals rule altogether in direct response. Maybe. Also a reminder of one of the key things that makes a Quad so very hard to pull off: football is really bloody daft.


Manchester City, 2020/21
Premier League: Won
FA Cup: Semi-finals
Champions League: Runner-up
League Cup: Won

No Spurs or Wigan whimsy this time around, with Chelsea proving to be City’s undoing on this occasion. That’s slightly less embarrassing, at least – it happened when the Blues were at least competent – but it did also occur twice.

The Quadruple has arguably never felt quite so feasible as it did on the morning of April 17 in 2021 when City, already in the Champions League last four and cruising to the league title with the Carabao safely in their pocket after Ryan Mason’s Spurs had been dealt with at Wembley, prepared to take on Chelsea in the FA Cup semi-final.

But a close-fought game was decided by Hakim Ziyech’s goal. As if that wasn’t enough, Chelsea would go on to repeat the punishment in the Champions League final in Porto six weeks later, Kai Havertz this time netting the only goal as City’s bid to land all four trophies ended with a mere and quite shameful two.


Liverpool, 2021/22
Premier League: Runner-up
FA Cup: Won
Champions League: Runner-up
League Cup: Won

Perhaps technically the closest a Premier League club has ever come to winning the Quadruple, Liverpool already had a pair of domestic trophies to show for their efforts as they entered a seismic final week, facing Wolves at home in the Premier League before continuing their perennial search for vengeance against Real Madrid in the Champions League.

Liverpool never were top of the Premier League on that remarkable last day but the opportunity was right there. With the gap to Manchester City at one point, Steven Gerrard had done his bit by guiding Aston Villa to a 2-0 lead at the Etihad as late as the 75th minute. But Pep Guardiola’s side maintained a slender advantage on goal difference for as long as Liverpool could not find a breakthrough against Wolves.

The Reds did eventually vanquish their obstinate visitors, but by the time Mo Salah and Andy Robertson scored in the 84th and 89th minutes to make it 3-1, Manchester City had already completed their remarkable turnaround with goals from Ilkay Gundogan and Rodri in the 76th, 78th and 81st minutes to lead Villa 3-2.

The Quadruple gone, those daft Reds went and lost 1-0 to Real Madrid six days later in another vain attempt to secure justice for Salah’s collarbone.


Manchester United, 2022/23
Premier League: No higher than third
FA Cup: Finalists
Europa League: Quarter-finalists
League Cup: Won

It was a genuine conversation and we shouldn’t pretend otherwise. Here’s to Manchester United and the single worst Quadruple tilt ever.


Manchester City, 2022/23
Premier League: Won
FA Cup: Won
Champions League: Won
League Cup: Quarter-finalists

There are two possible ways to view only the second proper Treble in English football: through the prism of a slightly larger number in those 115 charges; or by laughing at how Nathan Jones stood in the way of history being made.

Manchester City were kind enough to let Arsenal top the Premier League for most of the season before vanquishing the Gunners during a run of 12 consecutive and title-securing wins in one of Guardiola’s usual bouts of unstoppable post-Christmas form. The FA Cup was delivered a couple of weeks later with Manchester United beaten in the final, while seven days after that it was Inter who City just about managed to find a way past.

Three trophies were in the bag but it really ought to have been four. Then again, what is a trophy-hoarding machine supposed to do when encountering a relegation-bound team and one of the worst managers in Premier League history? Nathan Jones was in charge of Southampton for 95 days and a list of the five teams he beat before being sacked is just incredible: Everton (who sacked Frank Lampard nine days later), Crystal Palace (who sacked Patrick Vieira 70 days later), Lincoln (who were in the bottom half of League One), Blackpool (who would be relegated from League One) and an otherwise all-conquering City.


Liverpool, 2023/24
Premier League: Currently second, behind Arsenal on goal difference
FA Cup: Quarter-finalists
Europa League: Quarter-finalists, facing Atalanta
League Cup: Won

A traditional Quadruple – not that such a thing has been proven to actually exist or be possible – was never a prospect for a Liverpool side relegated to Europe’s secondary competition after their previous season’s hardship. They have at least enjoyed their Europa adventure and remain favourites to win the thing.

The hope will be to add that to the League Cup won by actual children and designated driver Virgil van Dijk against Chelsea at Wembley, while the Premier League title remains on the agenda with a single point separating the Reds, Arsenal and Manchester City heading into the final international break of the season.

But it will all be for nought as Jurgen Klopp’s final campaign at Anfield is forever bound to be tainted by yet another FA Cup defeat at Old Trafford – and the German losing his patience with one more reporter.

READ MOREThe many times Liverpool manager Jurgen Klopp has come across as a massive arse