Arsenal suffered a humiliating Carabao Cup fourth-round exit on Tuesday night after League Two Fleetwood Town defeated the Premier League champions on penalties at Highbury Stadium.
The Gunners recovered from Aaron Loupalo-Bi’s first-half opener through Viktor Gyokeres, but Max Dowman’s late dismissal compounded a frustrating evening for Arsenal manager Mikel Arteta.
Fleetwood goalkeeper Jay Lynch subsequently emerged as the hero, saving Bruno Guimarães’ penalty before Conor Haughey converted the decisive spot kick.
The evening began unusually, with a drone flying above the stadium forcing referee Michael Salisbury to suspend play for several minutes.
Arsenal dominated possession after the restart but struggled to create clear opportunities against Fleetwood’s organised defence.
The hosts capitalised in the 21st minute when Fulham loanee Loupalo-Bi turned Arsenal youngster Marli Salmon before finishing beneath Illan Meslier.
Despite fielding experienced attackers Kai Havertz and Gyokeres, Arsenal failed to establish any attacking rhythm during the opening period.
Havertz squandered their best first-half opportunity, heading over from close range after meeting a cross from Dowman.
Arteta responded at half-time by introducing Martin Odegaard and Ben White, with the Norwegian immediately improving Arsenal’s attacking movement.
The visitors eventually equalised when debutant Ceadach O’Neill produced an impressive run down the left before delivering for Gyökeres to convert.
Arsenal subsequently increased the pressure, with Odegaard controlling possession and creating openings against Fleetwood’s increasingly stretched defence.
However, Havertz failed to capitalise on further opportunities as the visitors struggled to turn their dominance into a second goal.
Eberechi Eze was introduced midway through the second half, adding another attacking option as Arsenal searched for a winner.
Fleetwood continued to defend resolutely, frustrating their Premier League opponents despite spending extended periods without possession.
Arsenal’s task became more difficult in the 86th minute when Dowman received a straight red card for kicking out at Harrison Neal following a challenge.
The 16-year-old’s dismissal left the Gunners with 10 men for the closing stages.
Nevertheless, Arsenal almost secured victory when White and Odegaard threatened late on, only for Lynch to produce outstanding saves.
The Fleetwood goalkeeper also denied Gyokeres in stoppage time, ensuring the contest proceeded to penalties.
Lynch then saved Guimarães’ effort in the shootout, allowing Haughey to seal a remarkable victory for the fourth-tier club.
Fleetwood’s triumph sparked jubilant celebrations and secured their place in the quarter-finals.
For Arsenal, the defeat ended their hopes of winning the competition for the first time since 1993, with attention now turning to Sunday’s Premier League trip to Liverpool.