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.
Recommended Betting Sites



- 18+. Min deposit £/€/$10 • A qualifying bet is a ‘real money’ stake of at least £/€/$10 • Min odds 1/2 (1.50) • Free Bets credited upon qualifying bet settlement and expire after 7 days • Free Bet stakes not included in returns • Casino Bonus must be claimed within 7 days • To withdraw bonus/related wins, wager the bonus amount 40 times within 14 days • Casino Bonus expires after 60 days • Withdrawal restrictions, payment methods, country & Full T&C’s apply. - Full Terms ApplyCreate your own Multiples with Bet BuilderLive Streaming of all UK & Irish RacingDaily Price Enhancements & Specialsnot requiredBonus Code
The code required to claim this sign-up bonus (if any)
Live StreamingIs there live streaming of sporting events?
YesIn-Play BettingThe number of sports with in-play betting available
16Bet BuilderCan you create your own personalised bets?
YesCash OutCan you cash out of bets before an event has finished?
YesAcca InsuranceRefund or free bet when one selection in an accumulator lets the bet down
Yes888sport offer a wide range of sports betting markets, combined with regular enhanced specials, plus an exclusive 'Acca Club' (bet £20 on Multiples or Bet Builder to get a £5 free bet - every week). - The Promotion operates as a £/€20 Surprise Bet when you place a bet of at least £/€10 on any market with odds greater than or equal to 1.50 as your first bet. The Promotion runs from 09/08/2021 / 12:00 (BST) until 31/12/2021 / 12:00 (BST) (the “Promotional Period”). The Promotion is only valid to: (a) new customers; (b) customers aged 18 years or over. To qualify for the Promotion, participant must deposit and place a £/€10 bet as their first bet on any market (excluding each way) in the sportsbook with odds greater than or equal to 1.50. Only original odds count toward the promotion. Supercharged odds do not count towards the promotion. An accumulation of smaller stakes will not count. Cashed out bets do not count towards this promotion. Only available once per customer. Rewards will be credited to qualifying participants within 48 hours after placing the qualifying bet. Potential winnings from the Surprise Bet are paid in withdrawable cash, excluding the stake. This offer cannot be used in conjunction with any other offer.Random Supercharged PayoutsWeekly ‘kwiff Club’ Cashback & Free Bets‘Acca Shield’ Refund (if One Leg Fails)not requiredBonus Code
The code required to claim this sign-up bonus (if any)
Live StreamingIs there live streaming of sporting events?
NoIn-Play BettingThe number of sports with in-play betting available
13Bet BuilderCan you create your own personalised bets?
NoCash OutCan you cash out of bets before an event has finished?
YesAcca InsuranceRefund or free bet when one selection in an accumulator lets the bet down
YesWhen a customer places a bet with kwiff, they may find that their bet is “kwiffed” - where you receive increased odds after placing your bet. - T&Cs apply. New customers on mobile only. 7 days to claim and stake £10 minimum bet at odds of 1.5 or greater to qualify. Free, void, cashed out or partially cashed out bets do not qualify. Max 3x £10 free bets credited on bet settlement. Free bets must be used on 4 or more selections with selection odds of 1.3 or greater. Free bets are non-withdrawable and stake not returned with winnings. 7 day expiry. 18+ BeGambleAware.orgWide Range of In-Play MarketsLive Streaming of UK Horse RacingBetting App for Android & iOS Devicesnot requiredBonus Code
The code required to claim this sign-up bonus (if any)
Live StreamingIs there live streaming of sporting events?
YesIn-Play BettingThe number of sports with in-play betting available
9Bet BuilderCan you create your own personalised bets?
YesCash OutCan you cash out of bets before an event has finished?
YesAcca InsuranceRefund or free bet when one selection in an accumulator lets the bet down
NoBetUK have leading National Hunt trainer Neil Mulholland and celebrity horse racing enthusiast and model Vogue Williams as brand ambassadors and betting experts. - T&Cs apply. New reg only. Claim by placing a min deposit £10 via "My Offers" page within 30 days. Skrill/Neteller deposits excl. 7 days to stake max £10 in-play. Max. extra winnings £100. 18+ BeGambleAware.org. - Full Terms ApplyMobile First Betting Interface'Leo King' Sports Prediction Game24/7 Customer Servicenot requiredBonus Code
The code required to claim this sign-up bonus (if any)
Live StreamingIs there live streaming of sporting events?
NoIn-Play BettingThe number of sports with in-play betting available
34Bet BuilderCan you create your own personalised bets?
YesCash OutCan you cash out of bets before an event has finished?
YesAcca InsuranceRefund or free bet when one selection in an accumulator lets the bet down
NoLeo Vegas Sports is the sportsbook from this multi-award-winning casino operator, with a focus on mobile users - including a sport betting app for Android & iOS Devices. - Min deposit requirement. Free Bets are paid as Bet Credits and are available for use upon settlement of bets to value of qualifying deposit. Min odds, bet and payment method exclusions apply. Returns exclude Bet Credits stake. Time limits and T&Cs apply. - Full Terms ApplyAwarded 'Sportsbook of the Year' 2018/19/20/21Live Streaming of 1000's of Events2 Goals Ahead Early Payout Offernot requiredBonus Code
The code required to claim this sign-up bonus (if any)
Live StreamingIs there live streaming of sporting events?
YesIn-Play BettingThe number of sports with in-play betting available
31Bet BuilderCan you create your own personalised bets?
YesCash OutCan you cash out of bets before an event has finished?
YesAcca InsuranceRefund or free bet when one selection in an accumulator lets the bet down
NoBet365 offer the most comprehensive online sports betting service, including live steaming of a huge range of sports, plus a unique 'Edit Bet' functionality. - 18+, Welcome Bonus: New Players only, 1st Deposit, Min Deposit,: £10, max £10 free bet valid for 14 days, bets must be placed at odds of 1/1 or greater and be settled within 14 days of placement. System bets not eligible. Neteller,Skrill and Paypal not eligible. T&Cs apply. Gamble responsibly. www.begambleaware.org'Rising Star Operator of the Year' 2021Interactive Football Match Centre‘BoostItOn’ Accumulator Boostsnot requiredBonus Code
The code required to claim this sign-up bonus (if any)
Live StreamingIs there live streaming of sporting events?
NoIn-Play BettingThe number of sports with in-play betting available
27Bet BuilderCan you create your own personalised bets?
NoCash OutCan you cash out of bets before an event has finished?
YesAcca InsuranceRefund or free bet when one selection in an accumulator lets the bet down
NoBetItOn have ex-Liverpool striker and Champions League winner Djibril Cissé as their brand ambassador and resident football expert. - 18+ new customers only. Opt in, bet £5 at odds 2.00+ within 7 days of registering, no cashout. Get 2x £10 Free Bets, set events at odds 2.00+. Plus £10 Slot Bonus, selected games, wager 20x to withdraw max £250. 7 day bonus expiry. Card payments only. T&Cs apply. begambleaware.org | Please gamble responsiblyLong Established UK BookmakerBV Loyalty Club - Weekly £5 Free BetFree to Play 'Pick 6' Predictor Gamenot requiredBonus Code
The code required to claim this sign-up bonus (if any)
Live StreamingIs there live streaming of sporting events?
YesIn-Play BettingThe number of sports with in-play betting available
12Bet BuilderCan you create your own personalised bets?
NoCash OutCan you cash out of bets before an event has finished?
YesAcca InsuranceRefund or free bet when one selection in an accumulator lets the bet down
NoBetVictor is named after founder Victor Chandler (known as the 'Gentleman Bookmaker') and they boast superstar jockey Rachael Blackmore, plus football legends Michael Owen and Harry Redknapp amongst their brand ambassadors and betting experts. - New customers. Max £10. 200% Odds Boost Token. Keep it fun - set your deposit limit. T&Cs apply. 18+. BeGambleAware.org'Million Pound Picks' Predictor GameLive Streaming of all UK & Irish Racing3 x Odds Boost Tokens Every Weeknot requiredBonus Code
The code required to claim this sign-up bonus (if any)
Live StreamingIs there live streaming of sporting events?
YesIn-Play BettingThe number of sports with in-play betting available
23Bet BuilderCan you create your own personalised bets?
YesCash OutCan you cash out of bets before an event has finished?
YesAcca InsuranceRefund or free bet when one selection in an accumulator lets the bet down
NoGrosvenor Sport is the sportsbook of Grosvenor Casinos - the UK's largest casino operator with over 50 casinos located in major towns and cities across the UK. - New players only. The qualifying bets to claim the Free Bet must have minimum odds of 3/1 (4.00) or higher and must be settled before triggering free bet. 18+. begambleaware.org - Full Terms Apply‘Jackpot Bets’ Syndicate BettingBet Builder & Live Betting FunctionalityClean & Easy to Navigate Interfacenot requiredBonus Code
The code required to claim this sign-up bonus (if any)
Live StreamingIs there live streaming of sporting events?
NoIn-Play BettingThe number of sports with in-play betting available
25Bet BuilderCan you create your own personalised bets?
YesCash OutCan you cash out of bets before an event has finished?
YesAcca InsuranceRefund or free bet when one selection in an accumulator lets the bet down
NoMr Green Sports is the sports betting offering from the award-winning Swedish casino operator, who offer both regular and syndicate betting (where you join forces with other players). - 18+ Eligible UK+IRE players. Paypal & some deposit & bet types excl. Min first £5 bet within 14 days of account reg at min odds 1/2 = 4x £5 free bets. Free bets valid for 7 days, stake not returned. No cashout, restrictions + T&Cs apply. - Full Terms ApplyOne of the UK's Biggest BookmakersFootball & Racing 'Super Series' Predictor Games'Beaten by a Length' Free Betsnot requiredBonus Code
The code required to claim this sign-up bonus (if any)
Live StreamingIs there live streaming of sporting events?
NoIn-Play BettingThe number of sports with in-play betting available
14Bet BuilderCan you create your own personalised bets?
NoCash OutCan you cash out of bets before an event has finished?
NoAcca InsuranceRefund or free bet when one selection in an accumulator lets the bet down
NoCoral has long established high street shops across the UK and with their industry-leading Coral Connect card you can deposit and withdraw money in shops, alongside a host of other benefits.
Stay In The Loop With Free Bets, Insider Tips & More!
Live Betting. Sports Promos. Sent Weekly.