Arsenal slumped to one of the biggest upsets in the English League Cup’s 66-year history, with the Premier League champion knocked out by fourth-tier Fleetwood Town in a penalty shootout in the last 16 on Tuesday.

Five months after losing on spot kicks to Paris Saint-Germain in the Champions League final, Arsenal endured more shootout misery — this time at the 5,300-capacity Highbury Stadium, the intimate home ground of Fleetwood that bears the same name as Arsenal’s storied former stadium.

Fleetwood — a team 84 positions further down the English soccer pyramid than Arsenal — converted all of its penalties and won the shootout 5-3. Arsenal’s Bruno Guimaraes saw his shot saved in the only failed attempt in the shootout.

The match finished 1-1 in regulation — with Arsenal ending it with 10 men after a red card for 16-year-old prodigy Max Dowman.

“A really sad day for us,” said Arsenal manager Mikel Arteta, who left out some first-team stars — like Declan Rice, Gabriel and David Raya — but still picked a strong lineup containing seasoned internationals.

Jubilant home fans streamed onto the field after Conor Haughey dispatched the clinching penalty for Fleetwood, which had never reached this stage of the competition before and — in 18th place in League Two — was the lowest-ranked club left in the draw.

“The biggest night in the club’s history in terms of opposition coming to town and we’ve managed to beat the (Premier League) champions,” Fleetwood manager Matt Lawlor said.

Fleetwood goalkeeper Jay Lynch, the star of the shootout after parrying aside Guimaraes’ attempt, said the team was inspired by another League Cup upset delivered by a fourth-tier side last season.

“We took heart from Grimsby beating Man United last year,” Lynch said. “We kind of compared it.

“Amazing for the club, the town. Honestly it means everything to everyone.”

Trailing to a 21st-minute strike by on-loan Fulham striker Aaron Loupalo-Bi, Arsenal threw on captain Martin Odegaard at halftime to get back into the match.

Viktor Gyokeres equalized in the 50th minute but Arsenal struggled to create many clear-cut chances after that and had Dowman sent off in the 85th for kicking out at an opponent who had floored him with a crunching tackle. Dowman appeared to get a rebuke from Arteta as he left the field.

“We have a massive responsibility to carry this badge in the best possible way,” Arteta said. “It had nothing to do with effort or application or determination to win it, but we lacked other things.”

Little-known Fleetwood is Jamie Vardy’s former club

Fleetwood, which is a coastal town in northwest England, is most famous for being the team where former England and Leicester striker Jamie Vardy made his name.

Vardy was there for just one season and helped Fleetwood gain promotion out of the fifth tier, and into the English Football League, before getting a move to Leicester in 2012.

In 2023, Fleetwood’s former owner, Andy Pilley, was handed a 13-year jail sentence for fraud. He lost an appeal in February this year.

Drone stops play

A drone hovering above the stadium caused an eight-minute delay soon after the match had kicked off.

Arsenal was about to take a free kick inside the second minute when the referee spotted the drone and temporarily stopped play, leading to jeers from some fans.

The referee spoke to the stadium safety officer, both managers and then some of the players before finally restarting the game.

More penalty pain for Guimaraes

Guimaraes should maybe stop taking penalties.

The midfielder had a spot kick saved in Brazil’s loss to Norway in the Round of 16 at the World Cup in the summer.

3rd-tier Bradford into the quarterfinals — and has pedigree

Bradford City will represent England’s third tier in the quarterfinals — 13 years after reaching the final of the competition when playing in the fourth tier.

Bradford beat Peterborough 2-0 and will join Fleetwood as the lower-league teams in Wednesday’s draw for the last eight.

In 2013, Bradford became the first fourth-tier team in more than 50 years to get to the final and lost 5-0 to Swansea at Wembley Stadium. It eliminated Arsenal on the path to the title match that season.

More matches on Wednesday

The last 16 continues on Wednesday with five more games, headlined by defending champion Manchester City at home to Brighton and Liverpool hosting Chelsea.

There are three more all-Premier League matchups: Bournemouth vs. Aston Villa, Fulham vs. Crystal Palace and Sunderland vs. Brentford.

On Thursday, Everton hosts Newcastle.

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Steve Douglas is at https://twitter.com/sdouglas80

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