The biggest FA Cup upsets ever

Wrexham goalscorers Steve Watkin and Mickey Thomas celebrate after their victory over Arsenal in the FA Cup, 1992
(Image credit: Getty Images)

The FA Cup is the greatest cup competition in football (or any sport, for that matter) and that’s thanks in no small part to its propensity for producing shock results.

Throughout its long and rich history, the FA Cup has been the stage for many a memorable giant-killing.

Here, we take a look at the biggest of them, with the only conditions being that they involved a top-flight team being knocked out by a side from at least two divisions below – and excluding finals, whose upsets warrant their own category.

Newport 2-1 Leicester (2018/19 third round)

Padraig Amond celebrates after scoring Newport County's winning goal, a penalty, against Leicester City in the FA Cup, 2019

Padraig Amond celebrates after scoring Newport's winning goal against Leicester (Image credit: Alamy)

Two seasons before winning their first FA Cup, Leicester suffered one of the most humiliating defeats in their history, going down away to fourth-tier Newport County.

The League Two side twice led their illustrious visitors – who fielded a rotated but nonetheless strong team – Padraig Amond sealing a famous triumph from the penalty spot on 85 minutes.

Stevenage 3-1 Newcastle (2010/11 third round)

Stevenage players celebrate after Michael Bostwick scored their second goal against Newcastle in the FA Cup, 2011

Stevenage players celebrate after Michael Bostwick scored their second goal against Newcastle (Image credit: Getty Images)

League Two Stevenage produced a memorable upset against Premier League Newcastle in relatively comfortable fashion.

The Hertfordshire outfit led 2-0 as the tie headed into stoppage time; Joey Barton pulled one back for the Magpies, who had Cheick Tiote sent off in the 71st minute, but – rather aptly – Peter Winn was on hand to make sure of victory moments later.

Oldham 3-2 Liverpool (2012/13 fourth round)

Matt Smith celebrates after scoring Oldham Athletic's first goal against Liverpool in the FA Cup, 2013

Matt Smith celebrates after scoring Oldham's first goal against Liverpool (Image credit: Alamy)

Oldham Athletic came out on the right side of a 3-2 thriller against Liverpool, Matt Smith bagging a brace on an incredible afternoon at Boundary Park.

The League One Latics held off the challenge of a Brendan Rodgers’ managed Reds team which featured the likes of Luis Suarez, Daniel Sturridge and Raheem Sterling from the start – and Steven Gerrard as a substitute.

Shrewsbury 2-1 Everton (2002/03 third round)

Nigel Jemson celebrates after scoring Shrewsbury Town's winning goal against Everton in the FA Cup, 2003

Nigel Jemson celebrates after scoring Shrewsbury's winning goal against Everton (Image credit: Alamy)

Shrewsbury Town sat some 80 places below Everton in the pyramid when they hosted the Premier League big boys at Gay Meadow – but they ran out deserved winners, captain Nigel Jemson notching both goals, the first with a brilliant free-kick.

The worst part for the Toffees? Shrewsbury were managed by Goodison Park legend Kevin Ratcliffe!

Manchester United 0-1 Leeds (2009/10 third round)

Jermaine Beckford scores Leeds United's winning goal against Manchester United in the FA Cup, 2010

Jermaine Beckford scores Leeds' winning goal against Manchester United (Image credit: Alamy)

A decade earlier, Leeds winning 1-0 at Old Trafford would have been a notable result but not an upset; in 2010, though, the Whites had fallen on hard times and were playing two divisions below their bitter rivals from across the Pennines.

But, midway through a season which saw them win promotion back to the second tier, they left Manchester United red-faced, Jermaine Beckford’s goal inflicting Alex Ferguson’s first FA Cup loss to lower-league opposition.

Birmingham 1-2 Altrincham (1985/86 third round)

Altrincham players celebrate after beating Birmingham City in the FA Cup, 1986

Altrincham players celebrate after beating Birmingham (Image credit: Alamy)

It was First Division vs fifth tier as Birmingham City hosted Altrincham in 1986 – and the visitors took the headlines with a significant giant-killing.

Birmingham, with 22-year-old David Seaman in goal, were downed by Kevin Ellis and an own goal by Robert Hopkins – who had earlier drawn the hosts level.

“I hope this result shakes things up and I can get some money from the board,” Blues manager Ron Saunders said after the game. He was sacked instead.

Norwich 0-1 Luton (2012/13 fourth round)

Scott Rendell celebrates after scoring Luton Town's winning goal against Norwich City in the FA Cup, 2013

Scott Rendell celebrates after scoring Luton's winning goal against Norwich (Image credit: Alamy)

Prior to their remarkable rise back up the pyramid, Luton Town were at their lowest ebb, playing in the fifth tier.

But the National League side weren’t fazed by the prospect of facing Premier League opposition away from home, and Scott Rendell’s 80th-minute strike made the Hatters the first non-League team to knock a top-flight side out of the FA Cup in 24 years.

Burnley 0-1 Lincoln (2016/17 fifth round)

Lincoln City players celebrate after Sean Raggett's winning goal against Burnley in the FA Cup, 2017

Lincoln players celebrate after Sean Raggett's winning goal against Burnley (Image credit: Getty Images)

The 2016/17 campaign was a hugely memorable one for Lincoln City, as they won promotion back to the Football League and reached the FA Cup quarter-finals – becoming the first non-League side to do so since 1914.

Having beaten Championship Ipswich and Brighton in the third and fourth rounds respectively, the Imps set up a dream last-eight tie against Arsenal as Sean Raggett’s 89th-minute header shocked Premier League Burnley at Turf Moor.

Bournemouth 2-0 Manchester United (1983/84 third round)

Milton Graham scores Bournemouth's first goal against Manchester United in the FA Cup, 1984

Milton Graham scores Bournemouth's first goal against Manchester United (Image credit: Alamy)

Some 26 years before that shock defeat to Leeds, Manchester United were stunned on the south coast.

Ron Atkinson’s Red Devils – boasting international stars such as Bryan Robson and Norman Whiteside – faced Third Division Bournemouth as FA Cup holders and sat second in the top flight – but a young Harry Redknapp masterminded one of the great giant-killings, Milton Graham and Ian Thompson scoring in the space of three second-half minutes.

Leicester 1-2 Wycombe (2000/01 quarter-finals)

Roy Essandoh celebrates with teammate Jason Cousins after scoring Wycombe Wanderers' winning goal against Leicester City in the FA Cup, 2001

Roy Essandoh celebrates with teammate Jason Cousins after scoring Wycombe's winning goal against Leicester (Image credit: Alamy)

Desperately searching for a fit striker who wasn’t cup-tied, Wycombe Wanderers turned to Ceefax (there was no social media in those days!).

Their call for help was answered by the agent of Roy Essandoh – who came off the bench to head in the winner for the Chairboys, then 16th in the third tier, away to Leicester, sixth in the Premier League.

Just to add to the drama, Wycombe boss Lawrie Sanchez was sent off and had to watch his team secure their remarkable upset on a TV in the dressing room.

Chelsea 2-4 Bradford (2014/15 fourth round)

Bradford City players celebrate after Mark Yeates scored their fourth goal against Chelsea in the FA Cup, 2015

Bradford players celebrate after Mark Yeates scored their fourth goal against Chelsea (Image credit: Alamy)

Jose Mourinho won his third Premier League title with Chelsea in 2015, but the Blues’ double hopes were dashed by League One Bradford City.

Bradford, who had reached the 2013 League Cup final as a League Two outfit, mounted an astonishing comeback to recover from 2-0 at Stamford Bridge against Petr Cech, Didier Drogba et al.

Walsall 2-0 Arsenal (1932/33 third round)

Arsenal manager Herbert Chapman pictured in 1932

Herbert Chapman was manager as Arsenal lost to Walsall (Image credit: Alamy)

Arsenal were just about the biggest club in the land at the start of the 1930s, winning two First Division titles in three years under the legendary Herbert Chapman – but they couldn’t get past Third Division North Walsall in the 1932/33 FA Cup.

The Gunners went on to be crowned champions of England that season, which only added to the magnitude of this upset.

Sutton 2-1 Coventry (1988/89 third round)

Sutton United players celebrate after beating Coventry City in the FA Cup, 1989

Sutton players celebrate after beating Coventry (Image credit: Getty Images)

Sutton United of the Conference went into this tie as 5,000/1 outsiders, while First Division Coventry had lifted the trophy just 18 months earlier.

But on a sandy pitch at Gander Green Lane, the non-League part-timers defied the odds to record an iconic FA Cup result, Matthew Hanlan’s volley just before the hour mark proving decisive.

Yeovil 2-1 Sunderland (1948/49 fourth round)

Yeovil Town vs Sunderland in the FA Cup, 1989

Yeovil vs Sunderland (Image credit: Alamy)

Non-League Yeovil Town shouldn’t have stood a chance against top-flight Sunderland – whose stars included British-record signing Len Shackleton – but the Somerset underdogs fought to pull off an amazing upset and reach the fifth round.

Captain Alec Stock had put Yeovil ahead in the first half, but Jackie Robinson equalised after the break and the tie went to extra time.

But the First Division favourites couldn’t complete the turnaround, and Eric Bryant was the match-winning hero for the Glovers.

Hereford 2-1 Newcastle AET (1971/72 third round replay)

Fans run onto the pitch as Ronnie Radford celebrates after scoring Hereford United's equalising goal against Newcastle United in the FA Cup, 1972

Fans run onto the pitch as Ronnie Radford celebrates after scoring Hereford's equaliser against Newcastle (Image credit: Alamy)

Ronnie Radford’s screamer for Hereford United against Newcastle sparked some of the most iconic scenes in FA Cup history, as fans flooded onto the pitch in celebration – but that goal wasn’t actually the winner.

That came from substitute Ricky George shortly before half-time in extra time – and precipitated similar pandemonium.

Following a 2-2 draw at St. James’ Park in the initial tie, this replay had been postponed several times due to a waterlogged pitch at Hereford’s Edgar Street, eventually taking place on the day of the fourth round itself.

Wrexham 2-1 Arsenal (1991/92 third round)

Wrexham goalscorers Steve Watkin and Mickey Thomas celebrate after beating Arsenal in the FA Cup, 1992

Wrexham goalscorers Steve Watkin and Mickey Thomas celebrate after beating Arsenal (Image credit: Alamy)

A whopping 81 league places separated Wrexham, 18th in the Fourth Division, and reigning champions of England Arsenal, seventh in the First Division, as they faced off at the Racecourse Ground.

It should have been a formality for George Graham’s Gunners, and things were going according to plan as Alan Smith gave them a half-time lead.

The hosts had other ideas, though, and quickfire goals from captain Mickey Thomas in the 82nd minute and Steve Watkin in the 84th flipped the tie well and truly on its head – and cued a full-time pitch invasion. The magic of the Cup.

Tom Hancock

Tom Hancock started freelancing for FourFourTwo in April 2019 and has also written for the Premier League and Opta Analyst, among others. He supports Wycombe Wanderers and has a soft spot for Wealdstone. A self-confessed statto, he has been known to watch football with a spreadsheet (or several) open...