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Arsenal's Carabao Cup campaign ended in disappointment after Premier League champions were eliminated by Fleetwood Town following a penalty shootout defeat at Highbury Stadium.
Mikel Arteta's side failed to overcome opponents ranked 84 places below them in the English football pyramid, surrendering their place in the competition's quarter-finals after a night of missed opportunities and late drama.
Fleetwood took the lead in the 21st minute through Aaron Loupalo-Bi, putting Arsenal under pressure against a team many would have expected them to defeat comfortably.
The Gunners eventually drew level after the break when Viktor Gyokeres scored, but the equaliser did not lead to a winning goal.
Arsenal struggled to make their chances count, allowing the hosts to remain in contention until the final stages.
Their task became more difficult in the 86th minute when teenage midfielder Max Dowman received a red card for kicking out after a heavy tackle by Harrison Neal.
Arsenal were forced to finish the contest with 10 men.
Despite their numerical disadvantage, the visitors had opportunities to avoid a shootout.
Fleetwood goalkeeper Jay Lynch, however, denied Ben White and Martin Odegaard late in the game, ensuring the tie remained level.
The penalty shootout proved decisive. Lynch saved Bruno Guimaraes' attempt before Conor Haughey converted the winning kick, sealing Arsenal's elimination and sending Fleetwood into the last eight.
The result brought an abrupt end to Arsenal's hopes of progressing further in the competition.
For Fleetwood, meanwhile, the victory represented a remarkable achievement against the reigning Premier League champions.
Arsenal must now turn their attention to their remaining commitments, while Fleetwood await the quarter-final draw, which will follow Wednesday's match between Chelsea and Liverpool.
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