OLIVER HOLT: Why Fleetwood beating Arsenal is the biggest Cup upset I've ever been to - and the rest of my top 10

Arsenal were stunned by League Two Fleetwood on Tuesday night, the champions of English football dumped out of the Carabao Cup by a team 84 places below them in the football pyramid.

Our Chief Sports Writer OLIVER HOLT was at Highbury to witness the giant-killing first-hand – and it ranks as one of the finest cup upsets he has seen in his career.

But how do Fleetwood's heroics compare to Lionel Messi being suckerpunched at the World Cup, or the comeback to end all comebacks in the Champions League final?

Read on to find out Oliver's verdict...

10. Manchester United 1 Porto 1 (2-3 on aggregate)

March 9, 2004. Champions League last 16 second leg, Old Trafford

This was a 1-1 draw at Old Trafford but it was enough to knock United out of the Champions League.

It was the match that put Jose Mourinho on the map when he ran half the length of the touchline to celebrate the late equaliser that put his team through and finished his sprint with a knee slide.

Porto went on to win the competition that season and Mourinho’s career was launched like a rocket.

United players react in disbelief after Costinha (not pictured) equalised for Porto in the 90th minute

Jose Mourinho announced himself in English football with his sprint down the Old Trafford touchline as his upstart Porto side went on to win the Champions League

9. Manchester United 3 Barcelona 0 (3-2 on aggregate)

March 21, 1984. Cup Winners' Cup quarter-final second leg, Old Trafford

Maybe it should never be an upset when a club of Manchester United’s size win a match but this was the Barcelona of Diego Maradona and United were 2-0 down from the first leg in Catalonia.

Inspired by Bryan Robson, United played like a whirlwind and swept Barcelona aside to win 3-0.

I was standing in the Stretford Paddock and it’s still one of the best atmospheres I’ve ever experienced at a football match.

Manchester United captain Bryan Robson exchanges pennants with Barcelona's Diego Maradona ahead of the second leg

The inspirational Robson scored twice to draw United level on aggregate, before Frank Stapleton's winning goal

8. Clyde 2 Celtic 1

January 8, 2006. Scottish Cup third round, Broadwood Stadium

The English press flocked to Clyde’s Broadwood stadium to watch this game because it was Roy Keane’s debut in Scottish football following his move from Manchester United. It didn’t go well.

Clyde stunned their mighty visitors and won 2-1. It was a sign of things to come for Keane north of the border.

The English press flocked to Clyde’s Broadwood stadium to watch this game because it was Roy Keane’s debut in Scottish football

Clyde's players led by captain Michael McGowan (centre) celebrate their historic victory over their mighty visitors

7. Manchester City 0 Wigan Athletic 1

May 11, 2013. FA Cup final, Wembley Stadium

City were just entering their period of dominance in the English game when they were beaten by relegation-threatened Wigan Athletic in the FA Cup final.

It was the first major trophy in Wigan’s existence and it was laden with emotion for their owner, Dave Whelan, who broke his leg playing for Blackburn Rovers in the 1960 FA Cup final against Wolves.

Whelan led the team out and watched them win courtesy of Ben Watson’s last-minute goal.

Wigan's Ben Watson heads in a late winner in the 2013 FA Cup final, shocking Man City as they were about to enter a period of dominance in English football

Watson (right) celebrates sending Wigan towards the first major trophy in their history

6. Stockport County 5 Bolton Wanderers 3 (AET)

November 17, 2021. FA Cup first round replay, Edgeley Park

Stockport were in the National League when they were paired with one of the old giants of the English game in the FA Cup. They drew the first tie in Bolton and then went 2-0 down inside six minutes with some kamikaze defending in the replay at Edgeley Park.

But then Paddy Madden scored a penalty, the comeback began, the ground turned into a bear-pit and the big boys from Bolton crumbled to a 5-3 defeat.

Ashley Palmer (5) powers in a header to bring Stockport back from the dead and send the tie to extra time

Scott Quigley (centre) struck five minutes into extra time to put Stockport in front

5. AC Milan 3 Liverpool 3 (AET, 2-3 on penalties)

May 25, 2005. Champions League final, Ataturk Olympic Stadium

Can you have a giant-killing in a Champions League final? Well, it felt like it when Liverpool worked the Miracle of Istanbul on AC Milan.

Liverpool’s starting line-up included Steve Finnan, Djimi Traore and Harry Kewell. Milan had Cafu, Paolo Maldini, Andriy Shevchenko, Kaka, Hernan Crespo and Andrea Pirlo.

Liverpool were embarrassed in the first half but they had the life-force that was Steven Gerrard and they came back from 3-0 down to effect the most stunning comeback in Champions League history.

Liverpool overcame a 3-0 deficit and an AC Milan superteam including Kaka, Paolo Maldini and Andriy Shevchenko (pictured) to win the 2005 Champions League final on penalties

Captain fantastic Steven Gerrard lifts the trophy after Jerzy Dudek's heroics in the shootout

4. Plymouth Argyle 1 Liverpool 0

February 9, 2025. FA Cup fourth round, Home Park

This had a Fleetwood-Arsenal vibe about it. I love going to Home Park. It’s another ground that feels like one of the outposts of the English game but it has the fanatical home support of the Green Army and one of the most handsome stands in the country, the Mayflower Grandstand.

Liverpool were on their way to winning the title under Arne Slot but he made 10 changes for this game and the Championship’s bottom club made him pay the penalty.

Liverpool were on their way to becoming Premier League champions when they travelled to Home Park in February 2025 - but a penalty from Ryan Hardie (second right) stopped them in their tracks

Then Plymouth boss Miron Muslic (centre) celebrates his side's remarkable victory in the home dressing room

3. Argentina 1 Saudi Arabia 2

November 22, 2022. World Cup group stage, Lusail Stadium

This felt like the end for Lionel Messi. I’m hoping most people have forgotten now, but I also wrote that it was the end. A few weeks later, he was lifting the World Cup for the first time.

That felt like a distant prospect after this humbling at the Lusail Stadium in Argentina’s opening game of the tournament. Messi had scored a penalty to put Argentina ahead but Saudi Arabia recovered to take a deserved 2-1 lead and win the game.

Messi looked tired and shot. It turned out he was just getting ready to prove everyone wrong.

Salem Al Dawsari's stunning winning goal condemned Argentina to defeat in their opening match, before they recovered to win their third World Cup title

2. England 1 Iceland 2

June 27, 2016. Euro 2016 last 16, Stade de Nice

Lagging only behind the 1-0 defeat by the USA in Belo Horizonte in 1950, this was England’s biggest humiliation in tournament football.

I remember arriving at the stadium in Nice and hearing and seeing the Viking Clap for the first time and getting a bad feeling as the Iceland fans went through their choreographed routine.

Once England went behind and the enormity of what was unfolding began to dawn on them, they froze. It was an abject humiliation.

Iceland's players react after knocking out Roy Hodgson's England at Euro 2016 - one of the biggest humiliations in the national team's history

Conor Haughey (left), the 19-year-old Northern Irish left back, celebrates after scoring the winning penalty in Fleetwood's giantkilling of Arsenal

1. Fleetwood Town 1 Arsenal 1 (5-3 on penalties)

October 27, 2026. League Cup fourth round, Highbury Stadium

Straight in at the top of my list. Nothing against Arsenal, who took the game seriously and behaved with class and dignity, but there was something life-affirming about being at Highbury Stadium on Tuesday night to see a team near the foot of League Two knock out the champions of England.

Fleetwood’s win on penalties summed up so much of the magic and the eccentricity of cup competitions in England. A drone delaying play, a gale raging through the stadium, a remote outpost of our game, a team that had not practised penalties scoring all five of their kicks, a stadium with a 5,000 capacity, a club whose fans are known as the Cod Army. It had everything.

At a time when there is so much cynicism in the English game, when Manchester City have been found guilty of serial cheating, this felt like an antidote.