League Two side Fleetwood Town have recorded one of the biggest upsets in the 66-year history of the Carabao Cup after eliminating Premier League champions Arsenal on penalties following a 1-1 draw on Tuesday.

Arsenal, who are separated from Fleetwood by 84 places in the English football pyramid, were unable to secure victory in regulation time before losing the penalty shootout, with £75m summer signing Bruno Guimarães missing the decisive kick.

The defeat sent Arsenal out of the competition in the last 16 and secured Fleetwood a place in the quarter-finals scheduled for December.

Fleetwood manager Matt Lawlor described the victory as the biggest night in the club’s history in terms of the opposition they faced.

“I just can’t believe it,” Lawlor told Sky Sports. “The biggest night in the club’s history in terms of opposition, and we’ve managed to beat the champions.”

Fleetwood take advantage of Arsenal’s struggles

The match, played at Fleetwood’s Highbury Stadium, was interrupted for more than eight minutes early in the first half after a drone flew over the pitch.

Arsenal struggled to impose themselves after play resumed and fell behind in the 21st minute when Aaron Loupalo-Bi, a 20-year-old striker on loan from Fulham, capitalised on a mistake by teenage defender Marli Salmon before finishing past goalkeeper Illan Meslier.

Despite dominating possession, the visitors found it difficult to break down Fleetwood’s defence during the first half.

Arsenal started several established first-team players, including Kai Havertz, Jurrien Timber, Viktor Gyökeres, Piero Hincapié, Myles Lewis-Skelly and Martin Zubimendi.

Manager Mikel Arteta introduced captain Martin Ødegaard and Ben White at half-time in an attempt to improve his side’s attacking play.

Arsenal eventually drew level in the 50th minute when Gyökeres bundled the ball over the line.

Eberechi Eze and Ezri Konsa were subsequently introduced as Arsenal searched for a winning goal, but the visitors failed to convert their possession and chances into another breakthrough.

Fleetwood remained organised defensively and held on to force the tie into a penalty shootout.

Dowman sent off as Arsenal exit

Arsenal’s hopes of recovering were further complicated in the 85th minute when 16-year-old Max Dowman received a straight red card.

The teenager was dismissed after reacting to a strong tackle by Fleetwood’s Harrison Neal. Television cameras later showed Arteta speaking sternly to the youngster as he walked towards the tunnel.

Asked by BBC Radio 5 Live what he told Dowman, Arteta said: “Something that we discussed already before the match.”

The defeat left the Arsenal manager disappointed, although he insisted that his players had not lacked commitment or determination.

“Attitude-wise, I have zero (issue). Otherwise, I would be here absolutely fuming. I’m sad, I think we are all sad. We have a massive responsibility to carry this badge in the best possible way,” he told Sky Sports.

He added that Arsenal had failed to create a sufficient margin despite the opportunities they produced.

“It had nothing to do with effort or application or determination to win it, but we lack other things to create a much bigger margin than today, with what we produce, they really should have been shown in the scoreline,” Arteta said.

Fleetwood celebrate landmark victory

Fleetwood, nicknamed the Cod Army because of the coastal town’s fishing heritage, entered the encounter after a difficult spell in League Two.

The club were 18th in the 24-team division and had lost their previous two league fixtures before hosting Arsenal.

Managed by 38-year-old Lawlor, a locally born former non-League player, Fleetwood have climbed through the English football pyramid over the past 15 years.

Their previous major achievement included reaching the League Two play-off final at Wembley in 2014. The club were relegated from League One in 2024.

Lawlor said his players understood the challenge of facing Arsenal and knew they would need to defend effectively rather than attempt to outplay their opponents.

“We knew before the game, we’re not stupid enough and not egotistical enough that you think we’re going to go to the best team in the country and the most organised team in the country — and the best of the basics and the world-class players — in that we’re going to go and outplay them,” he said.

“We had to ride our luck, we had to deny space, we had to deny options for them. We did that really, really well in terms of the majority of the game.”

The result represents another disappointing League Cup exit for Arsenal against lower-division opposition.

In December 2012, the north London club were eliminated by League Two Bradford City on penalties. They also suffered a 3-0 defeat against Championship side Sheffield Wednesday in October 2015.

Arsenal’s wait for another League Cup title will continue, while Arteta will now turn his attention to the Premier League fixture against Liverpool at Anfield on Sunday.

Fleetwood, meanwhile, are scheduled to host Bristol Rovers in their next match, although Lawlor admitted that the immediate celebrations would soon give way to preparations for their league campaign.

“I’ve just said to enjoy it, and then we’ve got a league game on Saturday, and I didn’t want to be the bearer of the reality, but we’ve got a game,” he said.