Where does Arsenal’s Fleetwood humiliation place in English cup shocks?

What the report says

Arsenal’s League Cup exit to fourth-tier Fleetwood Town has been framed by Al Jazeera as one of the major shocks in English football. The report says the Premier League champions were held to a 1-1 draw before losing 5-3 on penalties in the fourth round on Tuesday, a result that added their name to a long list of famous cup upsets.

The article uses the Fleetwood defeat as the starting point for a look back at other memorable surprises in English knockout football. It highlights earlier giant-killings involving clubs from lower divisions, including Wrexham’s 1992 FA Cup win over Arsenal, Bradford City’s comeback against Chelsea in 2015, and Hereford’s 1972 FA Cup victory over Newcastle United. It also points to Wimbledon’s 1988 FA Cup final win over Liverpool as one of the most striking examples of a smaller side overcoming a far stronger opponent.

A more recent comparison included in the piece is Grimsby Town’s penalty shootout victory over Manchester United in the 2025 League Cup. Al Jazeera presents these results as part of an ongoing debate over which upset deserves to be considered the biggest in English cup history, while noting that Arsenal’s defeat will now sit prominently in that conversation.