Arsenal's Quadruple Quest: A History of Dreams Derailed by Spurs, Wigan, Plymouth and Shambolic Managers

Arsenal currently occupy pole position in both the Premier League and Champions League, have one foot firmly planted in the Carabao Cup final, and command bookmakers' favour for the FA Cup. By any measure, this represents the most credible quadruple assault we've witnessed in years. Yet history teaches a brutal lesson: even when fortune smiles, the odds against sweeping all four remain preposterously steep.

The graveyard of fallen quadruple campaigns tells a cautionary tale littered with unexpected casualties and teams that settled for mere trophies like common underachievers.

Manchester United, 1998/99

Won: Premier League, FA Cup, Champions League

Fell at: League Cup quarter-final

Here's the thing about United's treble-winning season—nobody was even discussing a quadruple when they trudged to White Hart Lane in December 1998 to face Spurs in a League Cup quarter-final. They sat third, five points adrift of Aston Villa, hadn't kicked a ball in the FA Cup, and remained unproven in a Champions League group featuring Bayern Munich and Barcelona.

Yet apply hindsight and a butterfly effect logic, and you could construct a compelling case that this remains the closest anyone has come without realising it was happening. Yes, a gruelling two-legged semi against Wimbledon and a final against Leicester might have exhausted United's reserves—or perhaps not. They didn't lose once from December 19 onwards. In theory, they merely needed to dispatch teams who finished 11th, 16th and 10th. David Ginola, however, had other plans.

Arsenal, 2003/04

Won: Premier League

Fell at: FA Cup and League Cup semi-finals, Champions League quarter-finals

An unbeaten Premier League season is extraordinary. Finish with just one trophy and you've somehow managed to disappoint. Arsenal's Invincibles could have won all three cups—they were winnable prospects, genuinely.

Middlesbrough proved their executioners, dismantling the so-called Invincibles across a two-legged League Cup semi-final before claiming the trophy themselves. Manchester United blocked the FA Cup route at the semi-final stage. Chelsea delivered the Champions League coup, Wayne Bridge's 87th-minute strike at Highbury eliminating Arsenal in what proved a wide-open tournament ultimately won by Porto under Jose Mourinho. So much for invincibility.

Chelsea, 2006/07

Won: FA Cup, League Cup

Fell at: Premier League (2nd), Champions League semi-finals

Few quadruple bids have sustained momentum quite like Chelsea's 2006/07 campaign. Mourinho's resolute outfit pocketed the League Cup, reached the FA Cup final (which they'd subsequently win), battled Manchester United for the Premier League, and faced Liverpool in the Champions League semi-final.

After winning the first leg 1-0 at Stamford Bridge, Chelsea's hopes evaporated at Anfield. Daniel Agger's equaliser forced penalties where Arjen Robben and Geremi's misses proved decisive. Liverpool triumphed 4-1 on spot-kicks. The Blues then drew their final three Premier League matches, surrendering the title to Manchester United.

Manchester United, 2008/09

Won: Premier League, League Cup

Fell at: FA Cup semi-finals, Champions League final

A decade after Spurs derailed their previous quadruple dream, United exacted revenge by beating Tottenham on penalties in the League Cup final, with Ben Foster delivering heroics. The machinery then seized in April when Everton forced another goalless draw in the FA Cup semi-final, and United's shoot-out luck abandoned them.

United did secure the Premier League by winning eight of their final nine games—including that bewildering week when Federico Macheda became England's most essential footballer—but Barcelona schooled them comprehensively in the Champions League final. The real regret remains that FA Cup semi-final defeat.

Manchester City, 2013/14

Won: Premier League, League Cup

Fell at: FA Cup quarter-finals, Champions League last 16

City's obvious dominance sparked genuine quadruple speculation for the first time. Then Wigan happened. Having improbably denied City in the 2013 FA Cup final, the Latics returned a year later to humiliate them again, winning 2-1 at the Etihad in the quarter-final.

Barcelona completed the demolition job, winning 2-1 at Camp Nou after triumphing 2-0 in Manchester. City did win the league title with five consecutive victories and defeated Sunderland in the League Cup final, but Wigan had other ideas.

Manchester City, 2017/18

Won: Premier League, League Cup

Fell at: FA Cup fifth round, Champions League quarter-finals

Wigan struck again. The Latics somehow eliminated City in the FA Cup fifth round, denying them another domestic clean sweep. Liverpool then dismantled City's Champions League ambitions with a 3-0 demolition at Anfield followed by a 2-1 victory at the Etihad.

Manchester City, 2018/19

Won: Premier League, FA Cup, League Cup

Fell at: Champions League quarter-finals

Spurs delivered City's quadruple knockout blow in their own backyard. Having surrendered a 1-0 first-leg advantage almost instantly, Spurs stormed ahead through two Son Heung-min goals, establishing a two-goal cushion with away goals as insurance.

City roared back to lead 3-2 after barely 20 minutes of the second leg, only for Fernando Llorente to scramble home a controversial third Spurs goal to restore their away-goal advantage. City thought they'd won it again in stoppage time, but VAR's agonising check revealed an offside in the build-up. It was a night of such magnificent absurdity that UEFA subsequently abolished the away goals rule, partly in response to Spurs' bonkers Champions League trajectory. Spurs had become quadruple killers.

Manchester City, 2020/21

Won: Premier League, League Cup

Fell at: FA Cup semi-finals, Champions League final

Chelsea proved City's nemesis this time, appearing twice as their undoing. On April 17, 2021, with City already in the Champions League semi-finals and the league title seemingly secured, Hakim Ziyech's goal decided the FA Cup semi-final.

Six weeks later, Chelsea administered the final blow in Porto, Kai Havertz scoring the only goal in the Champions League final. City's quadruple bid concluded with a mere two trophies.

Liverpool, 2021/22

Won: FA Cup, League Cup

Fell at: Premier League (runner-up), Champions League final

Perhaps technically the closest any Premier League club has ventured toward the quadruple, Liverpool entered an extraordinary final week with two trophies secured, facing Wolves at home before confronting Real Madrid in the Champions League.

Steven Gerrard's Aston Villa led Manchester City 2-0 as late as the 75th minute. But City orchestrated a remarkable turnaround, goals from Ilkay Gundogan and Rodri (76th, 78th, 81st minutes) putting them ahead on goal difference. By the time Mo Salah and Andy Robertson scored for Liverpool against Wolves in the 84th and 89th minutes, City had already claimed the title.

Six days later, Real Madrid disposed of Liverpool 1-0 in another fruitless quest for European redemption.

Manchester United, 2022/23

Won: League Cup

Fell at: FA Cup final, Europa League quarter-finals, Premier League (3rd or lower)

This wasn't even a proper quadruple—it was a genuine if ridiculous conversation. United managed precisely one trophy. Even Spurs have won the Europa League.

Manchester City, 2022/23

Won: Premier League, FA Cup, Champions League

Fell at: League Cup quarter-finals

City claimed their second proper treble, though Nathan Jones somehow stood between them and history. The Southampton manager, sacked after 95 days, had spectacularly beaten Everton (who sacked Frank Lampard nine days later), Crystal Palace (sacked Patrick Vieira 70 days later), Lincoln, Blackpool, and an otherwise unstoppable City.

City had topped the Premier League for most of the season before vanquishing Arsenal during a 12-game winning streak in classic Guardiola December-onwards fashion. The FA Cup followed, then Inter in the Champions League final. Three trophies secured, though four should have been the destination.

Liverpool, 2023/24

Won: League Cup

Fell at: FA Cup quarter-finals, Europa League quarter-finals, Premier League (3rd)

When Liverpool lifted the Carabao, quadruple talk circulated with genuine foundation. They were Europa League favourites but exited prematurely. They were heavy FA Cup semi-final favourites against Manchester United but fell in the quarter-finals. The title race remained competitive until suddenly it wasn't.

Liverpool, 2024/25

Won: Premier League

Fell at: FA Cup fourth round, Champions League last 16, League Cup final (runner-up)

Arne Slot arrived and won the Premier League at a canter, precisely as predicted. Quadruple speculation naturally followed. Yet the dream perished in improbable fashion—a fourth-round FA Cup defeat to Championship basement-dwellers Plymouth. Given Liverpool's other commitments, the gamble was understandable. It backfired catastrophically.

Newcastle then administered a meek Carabao final defeat. The Champions League reward for topping the league stage was a PSG last-16 meeting. Liverpool somehow emerged from Paris with a 1-0 victory despite a fearful battering, only to lose 1-0 at Anfield before exiting on penalties.

They came closer to derailing PSG's knockout dominance than anyone—Aston Villa, Arsenal, and Inter were all dispatched—but those missed spot-kicks cost them dearly.