The English League Cup has long served as a battleground where football hierarchy collapses, carrying a rich history of lower-league sides humbling top-flight giants.

Arsenal’s elimination at the hands of fourth-tier Fleetwood Town on Tuesday, October 27, 2026, takes a prominent place in this storied legacy, widely regarded as one of the top three biggest upsets in the competition’s 66-year history.

Separated by a three-division gap and a massive gulf of transfer market value, the Premier League leaders became the first-ever top-flight leaders to fall to a fourth-tier side in the League Cup.

After Fleetwood took an early lead through Aaron Loupalo-Bi, Arsenal fought back to draw 1–1 before losing 5–3 on penalties following a late red card for Max Dowman.

This historic collapse joins an elite tier of legendary League Cup giant-killings that have stunned English football over the decades. In August 2014, Louis van Gaal’s Manchester United team was completely dismantled 4–0 by League One side MK Dons.

Arsenal (2013)

Arsenal themselves suffered another famous lower-league heartbreak in February 2013, when fourth-tier Bradford City eliminated them on penalties during an astonishing run that saw the Bantams reach the final at Wembley.

Among these historic shocks, the August 2025 clash between Manchester United and Grimsby Town stands out for its pure drama.

League Two outfit raced into a shocking 2–0 first-half lead at Blundell Park through Charles Vernam and Tyrell Warren, leaving the Premier League heavyweights reeling. The encounter saw Kenya defender Clarke Odupr make his debut for the club, and despite missing a penalty during the nerve-shredding shout-out, the minnows triumphed over United.

Late goals from Bryan Mbeumo and Harry Maguire in the 75th and 89th minutes forced a dramatic 2–2 draw, leading to an extraordinary penalty shootout. After all eleven players—including goalkeepers Christy Pym and André Onana—took kicks, Grimsby ultimately triumphed 12–11 on spot kicks to seal one of the most memorable nights in domestic cup history.