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15 Biggest Upsets in English League Cup History (Ranked)

Explore the most shocking upsets in English League Cup history, showcasing incredible moments that stunned football fans.

By Daniel Mawson · Give Me Sport

Published: Wednesday, 28 October 2026 at 2:48 PM

Key Things to Know

Daniel Mawson ranked the 15 biggest shock results and upsets in English League Cup history.
The list was prompted by League Two side Fleetwood Town knocking out reigning champions Arsenal on penalties.
Manchester United feature heavily, including aggregate defeats to York City in 1995 and a 4-0 loss to MK Dons.

The Story in 60 Seconds

GiveMeSport's Daniel Mawson ranked the biggest upsets in English League Cup history following Fleetwood Town's penalty shootout victory over Arsenal in October 2026. The ranking highlights notable occasions where lower-division underdogs eliminated elite top-flight opponents since the tournament's founding in 1960.

The featured shocks include York City eliminating Manchester United across two legs in 1995, MK Dons defeating United 4-0 in 2014, and Bradford City reaching the 2013 final after overcoming Aston Villa. Other entries include Sheffield Wednesday's 1991 final victory against United and Colchester United's 2019 shootout win over Tottenham.

Read the full article on Give Me Sport

15 Biggest Upsets in English League Cup History (Ranked)

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