Arsenal’s 5 biggest FA Cup upsets

The FA Cup may not be quite as special as it once was, but the competition’s magic will never dissipate.

Newcastle and Aston Villa were among the sides to succumb to the FA Cup’s dark arts over the weekend as they were upset by lower-league opposition. Villa’s defeat at home to Stevenage, a contest which they led 1-0 entering the 88th minute, was particularly stunning.

Arsenal will be hoping to avoid the voodoo nature of this competition when they take on League One side Oxford United on Monday night. The Gunners have suffered back-to-back early eliminations since winning the competition for the 15th time in 2020, but defeat at the Kassam Stadium would go down as one of FA Cup’s greatest-ever upsets.

Arsenal’s 5 biggest FA Cup upsets

No side has triumphed in this competition more than the Gunners, but the north London side have also been on the receiving end of some unforgettable upsets over the years. Here are five of the biggest.

Walsall 2-0 Arsenal (1933)

Ah yes, the great shock of ’33. I remember it well. For some (Walsall supporters), this is the greatest FA Cup upset of all time.

Herbert Chapman’s revolutionary Arsenal outfit were as mighty as they come, and they were expected to waltz beyond the Saddlers, then competing in the Division Three Northern Section, in this cup tie.

Chapman’s W-M-using Gunners were an immense counter-attacking outfit, but they came unstuck against the minnows in a stunning 2-0 defeat. Gilbert Alsop and Bill Sheppard grabbed second-half goals for Walsall against a rotated Arsenal side.

Tommy Black, who conceded the penalty which led to Walsall’s second goal, was reportedly told by the Chapman on the way home from the defeat to never be seen at Highbury again before he was sold to Plymouth the following week.

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