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World Sports

Southend United's Historic Upset Over Manchester United Remembered 20 Years On

Southend United's Historic Upset Over Manchester United Remembered 20 Years On
World Sports · 17:48:55 - Monday, 9 November 2026

Twenty years ago, on 7 November 2006, Southend United produced one of the most memorable upsets in English football by defeating Manchester United in the League Cup. The lower-league side toppled the Premier League giants at Old Trafford, a result that still resonates with fans of the Essex club.

The victory, achieved against a Manchester United team packed with international stars, remains a defining moment in Southend's history. Commemorations marking the anniversary highlight the enduring impact of that night, when the underdogs wrote themselves into cup folklore.

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