7 of Arsenal’s biggest embarrassments after shock EFL Cup exit to Fleetwood Town

Arsenal were dreaming of a quadruple until March last season, before losing the EFL Cup final. This time, there hasn’t even been time for any similar dreams to gain traction – they’ve been dumped out of the same competition in October.

And, shockingly, it was at the hands of Fleetwood Town, who are in the bottom half of League Two.

There’s no doubt Arsenal have been building back towards the glory days in recent times and their Premier League triumph last season was proof.

But Arsenal are a club that don’t really do things by halves. And they’ve had more than their fair share of embarrassing moments.

There’s something ironic about Arsenal getting knocked out of this season’s EFL Cup at Highbury Stadium.

Once upon a time, they’d win some and lose some at their own similarly-known venue. Fair enough. But losing at the home of a lowly League Two side is something else.

Mikel Arteta may have chucked in a couple of youngsters, but still named familiar faces like Viktor Gyokeres, Kai Havertz and Piero Hincapie into his starting XI.

And yet Fleetwood took the lead in the first half, with Arsenal only able to respond once in the second half.

Adding insult to injury, Max Dowman got sent off before the game went to penalties.

Bruno Guimaraes missed a vital penalty and Illan Meslier couldn’t save any as Fleetwood claimed a famous 5-3 shootout win.

Arsenal getting knocked out of the League Cup by a League Two team isn’t a totally new thing. Remember Bradford City?

Arsenal’s efforts in the 2012-13 fourth round had been bad enough. After going four goals down to Reading, they eventually had to fight back to win 7-5 after extra time.

Six weeks later, they headed north to Bradford for their quarter-final tie. Just 16 minutes in, they were already behind.

Thomas Vermaelen equalised, but only in the 88th minute. Thus, it went all the way through extra time and to penalties.

Vermaelen went from saviour to sinner, missing the crucial penalty that saw Arsenal eliminated.

Full credit to Bradford, who then knocked out Aston Villa before losing in the final to Swansea City. It’s a pathway Arsenal will have been kicking themselves over not being theirs.

There was an era when Arsenal and Manchester United were the two main powerhouses of English football. One or the other won all but one of the first 12 Premier League titles.

Both went on to suffer a decline in fortunes, but Arsenal’s started earlier – and they felt it painfully in 2011.

United slapped them with an 8-2 defeat, with Wayne Rooney scoring a hat trick. It was only 3-1 by half time, but things unravelled for Arsenal in the second half – even before a teenage Carl Jenkinson got sent off.

Close your eyes and you can picture the photos of the scoreboard after. One of the few Premier League games to have its own Wikipedia page.

One for the ages.

This one isn’t really about the result in itself, although there was more than a hint of embarrassment at conceding a stoppage-time penalty to draw with Birmingham City.

It’s what happened in the aftermath that has become most memorable: William Gallas’ tantrum.

After the full-time whistle, Gallas had a strop and sat down in the middle of the pitch. No one could get through to him for a good couple of minutes.

Eventually, he sensed Wenger coming and trudged off. All this after kicking the advertising hoardings earlier too, by the way, after giving away said penalty.

Gallas later apologised – well, kind of – but his sulk went down in Premier League folklore.

You simply have to marvel at Arsene Wenger’s longevity. Before he started bringing his madcap revolutionary ideas to FIFA, he served as Arsenal’s manager for more than 20 years.

But when his endurance should have been celebrated on the occasion of his 1,000th game in charge of Arsenal, he’ll instead have wanted to hide.

March 2014. Stamford Bridge. First versus third, this was Arsenal’s big chance to stay in the title race. But it was a complete disaster.

Arsenal were two goals down within seven minutes and a man down within 15. Things just went from bad to worse.

Even Mohamed Salah scored and he famously never did that for Chelsea.

A few years after the Gallas incident, Birmingham City were once again on the opposite end of an Arsenal embarrassment.

This time it was the 2011 League Cup final and after five seasons without a trophy, it looked like the perfect time for Arsenal to end their drought.

Fate had other ideas. Birmingham took the lead at Wembley through Nikola Zigic before Robin van Persie equalised.

There was to be an 89th-minute winner, but it wasn’t for Arsenal. Instead, Obafemi Martins scored to seal a memorable victory for Birmingham.

Arsenal must have been wondering when they’d taste glory again. They would have to wait until 2014 to win their next domestic cup.

Being thrashed 5-1 by Bayern Munich? It can happen. Twice in the space of three weeks, though? Ouch.

Arsenal have been working hard on their Champions League pedigree over Mikel Arteta’s reign and even reached the final last season.

But it hasn’t always been like that. In Wenger’s penultimate season, they were unceremoniously dumped out of the Champions League with a 10-2 aggregate defeat to Bayern.

They didn’t even qualify for the next Champions League either, so it was a disastrous way for Wenger to bid farewell to the competition.

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