Arsenal, the reigning Premier League champions and even Champions League finalists, are officially out of the Carabao Cup. Yeah, you read that right. They suffered a shock exit at the hands of Fleetwood Town, a League Two club sitting a whopping 84 places below them in the English football pyramid. Fleetwood pulled off one of the biggest upsets this competition has ever seen, beating Arsenal 5-3 on penalties after a wild 1-1 draw.
Fleetwood Town: From Underdogs to Giant Killers
This was truly the biggest victory in Fleetwood Town’s history, a moment for the club to absolutely savor. They stunned Arsenal, who you’d expect to roll over a fourth-tier club, right there at Highbury Stadium to reach the EFL Cup quarter-finals for the first time ever. Aaron Loupalo-Bi kicked things off in epic fashion, giving Fleetwood, 19th in their league, a 21st-minute lead. Arsenal’s Viktor Gyokeres pulled them level after the break, but then things got even spicier. The Gunners just couldn’t kick on, and their chances took a huge hit when their teenager Max Dowman got himself sent off in the 86th minute for kicking out after a challenge by Harrison Neal. Talk about drama! The game went to a shootout, and that’s where Fleetwood sealed it. Their keeper, Jay Lynch, was the hero, saving Bruno Guimaraes’ spot kick. Then Conor Haughey stepped up and buried the winning penalty, sparking pure pandemonium on the pitch and in the stands. What a moment for that club.
Where Does This Stack Up Against Other Iconic Cup Shocks?
So, where does Fleetwood beating Arsenal rank among the all-time great cup upsets? This isn’t just a regular surprise, it’s right up there with some legends. Let’s look at a few that come to mind.
Remember Grimsby Town versus Manchester United in the League Cup in 2025? Grimsby, another League Two side, beat top-flight Manchester United in a crazy 12-11 penalty shootout after a 2-2 draw. They were actually 2-0 up after only 30 minutes thanks to Charles Vernam and Tyrell Warren. United pulled one back through Bryan Mbeumo with 15 minutes to go, and then Harry Maguire leveled it at the 89th minute. The shootout was something else, with Clarke Oduor for Grimsby and Matheus Cunha for United being the only players to miss their first attempts. They went through all 11 players, then started over. Darragh Burns scored for Grimsby to make it 12-11, and then Mbeumo hit the crossbar on his second attempt. Absolutely wild.
Then there was Plymouth’s 1-0 FA Cup win over Liverpool in 2025. Liverpool, who would go on to win the Premier League title that season, paid the price for Arne Slot making 10 changes to his side. Eight minutes after halftime, Plymouth got a penalty from a Harvey Elliott handball, and Ryan Hardie absolutely drilled it home. Hardie almost grabbed a second, but Liverpool keeper Caoimhin Kelleher pushed his shot onto the post. The bottom club in the Championship held on, with Conor Hazard making some clutch late saves.
We also can’t forget Chelsea’s 2-4 FA Cup thrashing by Bradford City in 2015. Bradford was 49 places below Premier League leaders Chelsea when they rolled into Stamford Bridge. Chelsea was up 2-0 early with goals from Gary Cahill and Ramires. You’d think it was over, right? Nope. Jon Stead pulled one back, Filipe Morais equalized, Andy Halliday then blasted the Bantams ahead, and Mark Yeats slotted a fourth. Jose Mourinho’s side took a brutal beating that day.
And how about Oldham’s 3-2 FA Cup victory over Liverpool back in 2013? Premier League giants Liverpool had stars like Luis Suarez, Raheem Sterling, and Daniel Sturridge all starting, but financially struggling League One hosts Oldham produced a spirited display. Matt Smith nodded in a Youssouf M’Changama cross to open the scoring. Suarez leveled, but Smith capitalized on a Liverpool goalkeeper error and scored again. These are the games you just don’t forget.
So, Fleetwood reaching the League Cup quarter-finals for the first time by knocking out Premier League champions and Champions League finalists Arsenal? Yeah, that’s not just a footnote. That’s a massive, capital letters kind of upset. It’s one for the history books, and Fleetwood Town fans will be reliving that penalty shootout for years to come.
This article was created with AI assistance and published under Seattle On Tap’s editorial standards. See our Editorial Policy.
Originally reported by BBC Sport.
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