Five of the Biggest Betting Upsets in FA Cup History

From Bradford beating Jose Mourinho's Chelsea to Colchester beating Don Revie's Leeds, Gambling.com picks out our favourite ever FA Cup Betting upsets.

Colchester United 3-2 Leeds United, Fifth Round (1971)

Leeds were victims of one of the biggest FA Cup Final shocks in history when they were beaten 1-0 by Second Division Sunderland in 1973. Yet their defeat by Colchester two years earlier was even more eyebrow-raising, as Don Revie’s formidable side fell to a 3-2 loss at Layer Road.

Leeds arrived in Essex as favourites to win both the FA Cup and the First Division but departed with their tails firmly between their legs. Johnny Giles, Jack Charlton, Norman Hunter and Peter Lorimer were all part of a star-studded visiting side, although captain Billy Bremner was unavailable for selection for this fifth-round clash.

A quick-fire double from Ray Crawford put Colchester in dreamland after 25 minutes, before Dave Simmons further extended their advantage early in the second half. Goals from Hunter and Giles made for a nervy finish, but Colchester held on to send Revie’s mighty Leeds crashing out.

Wrexham 2-1 Arsenal, Third Round (1992)

George Graham described this defeat as his “lowest moment in football”, which goes some way to explaining how much of a shock Wrexham’s victory was.

The Fourth Division side were expected to be soundly beaten by a team containing Tony Adams, Paul Merson, Lee Dixon, David O’Leary, Alan Smith, David Seaman and David Rocastle, and their chances of clinging on for a replay were damaged when Smith gave the Gunners the lead in the 43rd minute.

Yet Arsenal were unable to find a second goal to put the game to bed, a failure for which they were made to pay late on. First, captain Mickey Thomas smashed a free-kick past Seaman to restore parity in the 82nd minute, before Steve Watkin punished a Nigel Winterburn mistake to take the roof off the Racecourse Ground.

Chelsea 2-4 Bradford City, Fourth Round (2015)

Perhaps the biggest shock of the modern era came at Stamford Bridge in 2015, although there was little sign of the script being ripped up after 38 minutes: Jose Mourinho’s side, who would go on to win the Premier League title a few months later, were 2-0 up at that stage of the match thanks to goals from Gary Cahill and Ramires.

With Didier Drogba, Petr Cech, Cesar Azpilicueta, Oscar and Mohamed Salah (whatever happened to him?) also on the pitch, the Blues seemingly had one foot in the fifth round before the interval.

Jon Stead halved the deficit for the League One side in the 41st minute, before a late flurry of goals turned the tie on its head. Cesc Fabregas and Willian had been introduced by the time Filipe Morais equalised with a quarter of an hour left to play, and Eden Hazard was thrown on immediately after that concession.

Not that it helped: goals from Andy Halliday and Mark Yeates completed an astonishing comeback for the Bantams, leading Mourinho to brandish his side’s exit a “disgrace”.

Sutton United 2-1 Coventry City, Third Round (1989)

In 2016/17 Sutton became only the ninth non-league team to reach the fifth round of the FA Cup since 1945. Their 1-0 defeat of Championship side Leeds United in the fourth round will live long in the memories of all those who witnessed it, but you have to go back to 1989 to find the greatest upset in the club’s history.

When Sutton, then in the Conference, were drawn against Coventry in the third round, the London outfit were determined to enjoy their big day out. And they certainly did that, as goals from captain Tony Rains and Matthew Hanlan either side of half-time gave United their most triumph of all time.

Coventry were a top-tier team who had won the competition two years earlier and whose starting XI featured several international players, but they came unstuck in front of 8000 fans at Gander Green Lane.

Hereford 2-1 Newcastle United, Third Round Replay (1972)

John Motson was just 26 years old when he was handed the microphone for Hereford’s third round replay against Newcastle in 1972. This was the first time many had heard the BBC commentator describe a game, and the stunning nature of the result did his career no harm whatsoever.

Fifth-tier Hereford had held top-flight Newcastle to a 2-2 draw in the original game, but the Magpies’ superior quality was expected to tell at Edgar Street. Malcolm Macdonald finally put the visitors in front with a header in the 82nd minute, but Ronnie Radford struck back with a superb 30-yard goal to level the scores and force extra time.

That equaliser seem to knock the stuffing out of Newcastle, and things got even worse when Ricky George gave Hereford an improbable lead in the 103rd minute. That strike prompted a pitch invasion from delirious Bulls fans, as the non-league side held on for a famous triumph which remains one of the most surprising in FA Cup history.