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The Express Gazette
Wednesday, October 28, 2026

Fleetwood's FA Cup Upset Ranked Among History's Greatest Shocks

Football writer Oliver Holt places Fleetwood's giant-killing of Arsenal at the pinnacle of cup upsets, drawing parallels to other historic footballing shocks.

US Politics • an hour ago
Fleetwood's FA Cup Upset Ranked Among History's Greatest Shocks

Football writer Oliver Holt has ranked Fleetwood's recent giant-killing victory over Arsenal as the greatest FA Cup upset he has personally witnessed. The columnist places this remarkable achievement at the very top of his personal list of footballing shocks, comparing its magnitude to other significant upsets in the sport's history.

Holt's assessment is not solely focused on Fleetwood's triumph but also contextualizes it against other memorable moments in football. He cites Lionel Messi's unexpected defeat at the World Cup and a dramatic Champions League final comeback as examples of the kind of seismic shifts that define the sport's most surprising outcomes.

While the article does not delve into the specifics of the Fleetwood-Arsenal match, it emphasizes the rarity and impact of such underdog victories. These moments, Holt suggests, are what elevate the FA Cup and football in general, offering narratives of defiance against overwhelming odds. The piece implies that Fleetwood's win has etched itself into the annals of sporting upsets, standing alongside other legendary shocks.

Other historic upsets mentioned in comparison include Stockport County's dramatic comeback against Doncaster Rovers, where Ashley Palmer's header sent the tie into extra time before Scott Quigley scored the winning goal. The article also references Wigan Athletic's 2013 FA Cup final victory over Manchester City, a win that defied expectations and occurred as City was establishing its dominance. Furthermore, it touches upon Plymouth's remarkable win under manager Miron Muslic and the legendary comeback orchestrated by Liverpool against AC Milan in the Champions League final, fueled by Steven Gerrard's leadership and Jerzy Dudek's goalkeeping heroics. The debut of Roy Keane in Scottish football for Clyde, a highly anticipated event covered by the English press, is also noted as a significant moment, even if not an upset in the same vein. The legendary encounter between Manchester United and Barcelona, featuring Diego Maradona, and a notable victory by Manchester United captain Bryan Robson, are also brought into the historical context of significant footballing events.


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