Ranking biggest FA Cup upsets this century: Liverpool ousted by Plymouth Argyle, Man City shock final defeat

There’s a reason the phrase “the magic of the FA Cup” gets as much usage as it does – the English competition likes to deliver an upset every now and again, making for an enjoyably long list of games when the underdog triumphed over the overwhelming favorites.The FA Cup offers somewhat rare occasions for top-tier sides to meet teams much further down the soccer pyramid, and the even rarer chance for those lower-league sides to get the better of their flashy opponents in a one-off. The most recent instance came in this season’s fourth round when Championship bottom-dwellers Plymouth Argyle managed a surprise win over Premier League leader Liverpool and came out with a result that ranks amongst the most notable games in the FA Cup’s recent history.  

Let’s take a look back at one shocking upset that included Wrexham before we rank the best modern-day upsets that came after the turn of the century:

Honorable throwback: Wrexham 2, Arsenal 1 (1992)

Decades before Wrexham became Hollywood royalty, the Wales-based outfit were partly on the English soccer map thanks to their 1992 FA Cup shock win over Arsenal. The Gunners led with 10 minutes to go at the Racecourse Ground and the hosts — bottom of the fourth tier at the time — miraculously fought back to win through a veteran Mickey Thomas free kick and a famous late winner through Steve Watkin to doom the Londoners.

Honorable mention: Newport 2, Leicester 1 (2019)

There were 74 places between these two sides six years or so ago and Leicester City had been EPL champions not that long ago. Rodney Parade hosted a proper third-round tier in early January with Padraig Amond’s late penalty enough to stun the Foxes and give the Wales-based hosts a famous first topflight win since 1963-64.

Honorable mention: Plymouth Argyle 1, Liverpool 0 (2025)

This season’s edition of the FA Cup has already added a new contender to the list, with Plymouth Argyle’s win over Liverpool in the fourth round serving as one of the more memorable upsets in recent years. The Reds were atop the Premier League coming into this one, in the midst of a near-perfect first season under manager Arne Slot, while Plymouth were dead last in the Championship, in part doomed by a short but damaging managerial spell for Wayne Rooney. It was Plymouth, under new manager Miron Muslic, who came out on top and came out with a win against a rotated Liverpool team, who managed just four shots in the first 70 minutes and delivered little in terms of quality throughout.

Now we look at some of the most memorable upsets since 2000:

5. Lincoln City 1, Burnley 0 (2017)

The Imps made history as the first non-league side to reach the FA Cup quarterfinals in over 100 years (since 1914) when the Cowley brothers inspired a stunning win over the Clarets. Sean Raggett’s dramatic headed goal with Lincoln’s only shot on target also required goal line technology confirmation before it was given.

4. Wigan 1, City 0 (2013)

A classic FA Cup final upset arrived 12 years ago when Ben Watson’s late, late header ensured that the Latics beat giants City to cap an incredible cup run. Roberto Martinez inspired the side to their first-ever major trophy in English soccer at the same time that they were being relegated from the Premier League.

3. Southampton 1, Grimsby Town 2 (2023)

The Mariners made history two years ago with a 2-1 win over the Saints to reach the quarterfinals for the first time since 1939. Two penalties either side of the break ensured that Grimsby survived a late disallowed home goal to eliminate a team 64 places above them in the English soccer pyramid. It was also the first time in 152 that that a team knocked out five teams from higher leagues in the same cup run having already dumped Plymouth Argyle, Cambridge United, Burton Albion and Luton Town out despite their fourth-tier status.

2. Crawley 3, Leeds 0 (2021)

One of the FA Cup’s most astonishing results came four years ago when Marcelo Bielsa’s men were in the Premier League and fell victim to League Two Crawley despite a 62-team chasm between the two. Broadfield witnessed a 20-minute blitz in the second half and even saw a reality TV star sent on as a substitute in the dying minutes in a game that had a bit of everything.

1. Chelsea 2, Bradford 4 (2015)

Top of the pile, though, has to be a fightback from two goals down to knock EPL giants Chelsea out 10 years ago by thirdtier Bradford. The Blues opened up a two-goal lead at Stamford Bridge only to concede four times as the Bantams made light of their 49-team difference between the two thanks to goals from Jon Stead, Filipe Morais, Andy Halliday and Mark Yeates to beat Jose Mourinho’s men to the quarterfinals in the most unlikely of circumstances.