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Biggest FA Cup Upsets Based on the Gap in the League Pyramid

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Wrexham vs Arsenal 2-1 (1992)

Finishing bottom of the entire Football League the previous season, Wrexham escaped the clutches of relegation solely due to the expansion of the Football League and were expected to just drop straight back down.

In polar opposite circumstances, Arsenal celebrated winning the First Division in the season prior, losing just one game in the process making the London side overwhelming favourites in this one and creating a potential upset of the greatest calibre.

Thanks to an Alan Smith free-kick, the Gunners looked to be progressing into the next round with 10 minutes to go, however, the tie rapidly turned on its head as a free-kick from Mickey Thomas saw the host’s go level. Two minutes later, madness ensued as the Welsh side took the lead as George Graham’s side crashed out the cup in the third round in what he described as his darkest day in management.

Given the contrasting sides and how Arsenal were England's kings back then, it's arguably the biggest upset there's ever been.

Sutton United vs Coventry City 2-1 (1989)

Having lifted the FA Cup just two years prior and sitting firmly in England’s top division of football, Coventry City travelled to Gander Green Lane to face non-league Sutton United.

Tony Raines gave the home side a lead heading into the break, however, Coventry’s David Phillip’s levelled the scoring as the visitors looked to be turning the tie around. Sutton United, who boasted not one full-time player, found the winner late on as Matthew Hanlan turned in a close-range effort following a corner.

This game went down in history as a true giant-killer, as Barrie Williams side handed the Sky Blues a surprise early exit from the tournament.

Shrewsbury vs Everton 2-1 (2003)

A mammoth 80 places below David Moyes’ Everton side, Shrewsbury Town welcomed the Toffees at Gay Meadow in a match that quickly entered the history books. Managed by Everton legend, Kevin Ratcliffe, the Shrews dominated the visitors who included the likes of Thomas Gravesen and a 17-year-old Wayne Rooney.

England and Everton goalkeeper Richard Wright did well to keep the game goalless with a string of excellent saves, however, Shrews captain Nigel Jerson gave the home side a well-deserved lead before heading into the break.

Everton equalised on the hour but with just two minutes left to play, Jerson had the ball in the net again to send the Toffees home in dismay after failing to tame the Shrews.

Norwich vs Luton Town 0-1 (2013)

If this match took place tomorrow, the result could go either way without the general footballing world batting an eyelid, however, back in 2013, 85 places separated these two sides as Luton Town were on the brink of complete financial disaster.

Norwich came close but efforts from Leon Barnett, Simeon Jackson, and a young Harry Kane all failed to break the deadlock in the first half.

The Hatters remained steadfast after the break and just 10 minutes from time, substitute Scott Rendell saw his effort beat Canaries keeper Declan Rudd in what was to be the only goal of the game. The home side were unlucky not to be awarded a late spot-kick as Luton’s Lathaniel Rowe-Turner handled the ball in his own penalty area, however, it was missed by referee Andre Mariner.

Nevertheless, the Hatters held on and became the first non-league side to knock out a Premier League opponent in the competition's history and it's one of the biggest upsets based solely off distance within the league pyramid.

Hereford vs Newcastle 2-2 & 2-1 (1972)

For the final entry, it’s a two-for-one upset, as Southern League outfit Hereford stunned Newcastle United not once but twice. Following a 2-2 draw at St. James' Park - which in itself was a major shock - Hereford welcomed First Division giants Newcastle United to Edgar Street where in truth, they surely expected to see their FA Cup magic run out.

Malcolm McDonald gave the away side a lead with just 10 minutes to go before a late thunderstrike by Ronnie Radford took the game into extra time. The Magpies squandered a good chance to retake the lead before Ricky George scored the goal that sealed the Hereford name in the history books as the home crowd flooded the pitch.

This game is true, raw, FA Cup magic and can still be regarded as one of the famous upsets in domestic football history, and perhaps the most memorable in the FA Cup history books.

Peterborough United vs Chorley 1-2 (2020)

In a more recent cup upset, Peterborough United welcomed non-league Chorley who had knocked out former winners Wigan Athletic in the previous round courtesy of extra-time.

Just two minutes in, the home side capitalised from a set-piece as Jack Taylor rifled in a superb half-volley to give the Posh side a lead. On the hour mark, forward Connor Hall levelled the scoring, and minutes later, teammate Lewis Baines added a second after a poorly defended corner.

Besides a missed penalty, the hosts created little in the remaining 30 minutes as non-league Chorley and being managed by schoolteacher Jamie Vermiglio, they taught Peterborough a lesson they won’t forget quickly. 89 places separated these two sides prior to kick-off making this mathematically the biggest FA Cup shock of the campaign.