Five of the Biggest Betting Upsets in FA Cup History

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.


Check Out: FA Cup Betting Offers

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

Bell Icon
Affiliate Disclosure: At Gambling.com, we want to ensure that players are matched with the right casino and sportsbook offers for them. For this reason, some of the recommended site links are affiliate links. This means that if you visit a website through our link and make a deposit, Gambling.com will receive a commission payment at no extra cost to you. At Gambling.com, we want to ensure that players are matched with the right casino and sportsbook offers for them. For this reason, some of the recommended site links are affiliate links. More
  1. 1
    Hey Spin Sports
    Established 2020
    More Details
    Dual Sportsbook & Casino Platform
    Extensive Range of Football Markets
    Accumulator Boosts of up to 77%
    Bonus Code
    The code required to claim this sign-up bonus (if any)
    not required
    Live Streaming
    Is there live streaming of sporting events?
    No
    In-Play Betting
    The number of sports with in-play betting available
    18
    Bet Builder
    Can you create your own personalised bets?
    Yes
    Cash Out
    Can you cash out of bets before an event has finished?
    Yes
    Acca Insurance
    Refund or free bet when one selection in an accumulator lets the bet down
    No
    Heyspin is an online betting site that offers both sports betting and online casino games. Their impressive sportsbook platform offers a huge range of markets, including in-play betting and cash-out options.
  2. 2
    Luckster Sports
    Established 2022
    More Details
    Live Betting & Cash-Out Options
    Well Designed & Easy To Use Interface
    ‘Boost Up’ Accumulator Boosts
    Bonus Code
    The code required to claim this sign-up bonus (if any)
    not required
    Live Streaming
    Is there live streaming of sporting events?
    No
    In-Play Betting
    The number of sports with in-play betting available
    12
    Bet Builder
    Can you create your own personalised bets?
    No
    Cash Out
    Can you cash out of bets before an event has finished?
    Yes
    Acca Insurance
    Refund or free bet when one selection in an accumulator lets the bet down
    No
    Luckster is a dual sportsbook and casino platform with a vaguely Irish theme, including the inevitable leprechaun logo and shamrock imagery.
  3. Brand Ambassador Teddy Sheringham
    Live Streaming of UK Horse Racing
    Acca Club: £5 Free Bet Every Week
    Bonus Code
    The code required to claim this sign-up bonus (if any)
    not required
    Live Streaming
    Is there live streaming of sporting events?
    Yes
    In-Play Betting
    The number of sports with in-play betting available
    9
    Bet Builder
    Can you create your own personalised bets?
    Yes
    Cash Out
    Can you cash out of bets before an event has finished?
    Yes
    Acca Insurance
    Refund or free bet when one selection in an accumulator lets the bet down
    Yes
    BetUK have former England footballer Teddy Sheringham and six time champion jockey Kieren Fallon as brand ambassadors and betting experts.
  4. 4
    Zet Bet Sports
    Established 2022
    More Details
    Fast & Clean Betting Interface
    'Zet Boost' Accumulator Boosts
    Broad Range of Sports & Esports Markets
    Bonus Code
    The code required to claim this sign-up bonus (if any)
    not required
    Live Streaming
    Is there live streaming of sporting events?
    No
    In-Play Betting
    The number of sports with in-play betting available
    21
    Bet Builder
    Can you create your own personalised bets?
    No
    Cash Out
    Can you cash out of bets before an event has finished?
    Yes
    Acca Insurance
    Refund or free bet when one selection in an accumulator lets the bet down
    No
    ZetBet is a new to market UK betting site that includes an attractive sportsbook with excellent filters to enable you to find your bet quickly and easily.
  5. UK's Leading Horse Racing Pool Betting Operator
    Home of the Placepot & Exclusive Placepot App
    Never Beaten by SP on Horse Racing with Tote+
    Bonus Code
    The code required to claim this sign-up bonus (if any)
    not required
    Live Streaming
    Is there live streaming of sporting events?
    Yes
    In-Play Betting
    The number of sports with in-play betting available
    2
    Bet Builder
    Can you create your own personalised bets?
    No
    Cash Out
    Can you cash out of bets before an event has finished?
    No
    Acca Insurance
    Refund or free bet when one selection in an accumulator lets the bet down
    No
    The Tote offers horse racing pool betting, popular with punters who place small stakes to win large amounts. Favourite bets include the Placepot (picking a horse to be placed in the first six races) and Jackpot/Scoop6 (picking the winner of each of six nominated races on a single day).
  6. Long Established Independent Bookmaker
    Unique Horse Racing Free Bet Refunds
    Racing Ambassadors Hayley Turner & Tom Cannon
    Bonus Code
    The code required to claim this sign-up bonus (if any)
    not required
    Live Streaming
    Is there live streaming of sporting events?
    No
    In-Play Betting
    The number of sports with in-play betting available
    10
    Bet Builder
    Can you create your own personalised bets?
    Yes
    Cash Out
    Can you cash out of bets before an event has finished?
    Yes
    Acca Insurance
    Refund or free bet when one selection in an accumulator lets the bet down
    No
    Betgoodwin is the new online betting site from the independently owned Goodwin Racing telephone betting service. They offer a variety of horse racing special offers as well as betting on a variety of other sports.
  7. 7
    Kwiff Sports
    Established 2015
    More Details
    Random Supercharged Payouts
    Weekly ‘kwiff Club’ Cashback & Free Bets
    ‘Acca Shield’ Refund (if One Leg Fails)
    Bonus Code
    The code required to claim this sign-up bonus (if any)
    not required
    Live Streaming
    Is there live streaming of sporting events?
    Yes
    In-Play Betting
    The number of sports with in-play betting available
    13
    Bet Builder
    Can you create your own personalised bets?
    No
    Cash Out
    Can you cash out of bets before an event has finished?
    Yes
    Acca Insurance
    Refund or free bet when one selection in an accumulator lets the bet down
    Yes
    When a customer places a bet with kwiff, they may find that their bet is “kwiffed” - where you receive increased odds after placing your bet.
  8. Official UK Betting Partner of Fulham FC
    Regular Money-Back Specials
    'Racing Sportsbook of the Year' 2020
    Bonus Code
    The code required to claim this sign-up bonus (if any)
    not required
    Live Streaming
    Is there live streaming of sporting events?
    No
    In-Play Betting
    The number of sports with in-play betting available
    8
    Bet Builder
    Can you create your own personalised bets?
    Yes
    Cash Out
    Can you cash out of bets before an event has finished?
    Yes
    Acca Insurance
    Refund or free bet when one selection in an accumulator lets the bet down
    No
    Fitzdares have offered a boutique bookmaker service to members of their exclusive Mayfair Club (The Fitzdares Club) since 1882, but have now launched an online sportsbook open to all.
  9. Mobile First Betting Interface
    'Leo King' Sports Prediction Game
    24/7 Customer Service
    Bonus Code
    The code required to claim this sign-up bonus (if any)
    not required
    Live Streaming
    Is there live streaming of sporting events?
    Yes
    In-Play Betting
    The number of sports with in-play betting available
    34
    Bet Builder
    Can you create your own personalised bets?
    Yes
    Cash Out
    Can you cash out of bets before an event has finished?
    Yes
    Acca Insurance
    Refund or free bet when one selection in an accumulator lets the bet down
    No
    Leo 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.
  10. Create Your Own Accumulater with 'Bet Maker'
    Enhanced Odds Every Week with 'BetPlus'
    Live Streaming of International Horse Racing
    Bonus Code
    The code required to claim this sign-up bonus (if any)
    not required
    Live Streaming
    Is there live streaming of sporting events?
    No
    In-Play Betting
    The number of sports with in-play betting available
    34
    Bet Builder
    Can you create your own personalised bets?
    Yes
    Cash Out
    Can you cash out of bets before an event has finished?
    Yes
    Acca Insurance
    Refund or free bet when one selection in an accumulator lets the bet down
    Yes
    Well known in Europe and growing fast in the UK, NetBet offer some unique features, such as 'Snap Bet' - where mobile users can bet on a goal being scored in the next 30 secs, 1 min, 5 mins or 10 mins of live football matches.
  11. 11
    888 Sports
    Established 1997
    More Details
    Create your own Multiples with Bet Builder
    Live Streaming of all UK & Irish Racing
    Daily Price Enhancements & Specials
    Bonus Code
    The code required to claim this sign-up bonus (if any)
    not required
    Live Streaming
    Is there live streaming of sporting events?
    Yes
    In-Play Betting
    The number of sports with in-play betting available
    16
    Bet Builder
    Can you create your own personalised bets?
    Yes
    Cash Out
    Can you cash out of bets before an event has finished?
    Yes
    Acca Insurance
    Refund or free bet when one selection in an accumulator lets the bet down
    Yes
    888sport 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).
  12. 12
    BetItOn Sportsbook
    Established 2020
    More Details
    'Rising Star Operator of the Year' 2021
    Interactive Football Match Centre
    ‘BoostItOn’ Accumulator Boosts
    Bonus Code
    The code required to claim this sign-up bonus (if any)
    not required
    Live Streaming
    Is there live streaming of sporting events?
    No
    In-Play Betting
    The number of sports with in-play betting available
    27
    Bet Builder
    Can you create your own personalised bets?
    No
    Cash Out
    Can you cash out of bets before an event has finished?
    Yes
    Acca Insurance
    Refund or free bet when one selection in an accumulator lets the bet down
    No
    BetItOn have ex-Liverpool striker and Champions League winner Djibril Cissé as their brand ambassador and resident football expert.
  13. 13
    mr.play Sports
    Established 2017
    More Details
    Dual Sportsbook & Casino Platform
    Distinctive ‘Moustache’ Branding
    ‘PlayBoost’ Accumulator Boosts
    Bonus Code
    The code required to claim this sign-up bonus (if any)
    not required
    Live Streaming
    Is there live streaming of sporting events?
    No
    In-Play Betting
    The number of sports with in-play betting available
    21
    Bet Builder
    Can you create your own personalised bets?
    No
    Cash Out
    Can you cash out of bets before an event has finished?
    Yes
    Acca Insurance
    Refund or free bet when one selection in an accumulator lets the bet down
    No
    Mr.Play Sports has a fun style of its very own, with a memorable handlebar 'tache wherever you look, but it boasts a serious amount of betting markets, plus Premier League & 'Euro Elite' betting battle tournaments.
  14. 14
    BetVictor Sports
    Established 1946
    More Details
    Long Established UK Bookmaker
    BV Loyalty Club - Weekly £5 Free Bet
    Free to Play 'Pick 6' Predictor Game
    Bonus Code
    The code required to claim this sign-up bonus (if any)
    not required
    Live Streaming
    Is there live streaming of sporting events?
    Yes
    In-Play Betting
    The number of sports with in-play betting available
    12
    Bet Builder
    Can you create your own personalised bets?
    Yes
    Cash Out
    Can you cash out of bets before an event has finished?
    Yes
    Acca Insurance
    Refund or free bet when one selection in an accumulator lets the bet down
    No
    BetVictor 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.
  15. 15
    10bet Sports
    Established 2003
    More Details
    Regular Free Bets & Enhanced Odds Specials
    Cutting Edge In-Play Betting Options
    Accumulator Boosts of up to 50%
    Bonus Code
    The code required to claim this sign-up bonus (if any)
    not required
    Live Streaming
    Is there live streaming of sporting events?
    No
    In-Play Betting
    The number of sports with in-play betting available
    12
    Bet Builder
    Can you create your own personalised bets?
    Yes
    Cash Out
    Can you cash out of bets before an event has finished?
    No
    Acca Insurance
    Refund or free bet when one selection in an accumulator lets the bet down
    No
    10bet is one of the smaller online bookmaker brands in the UK but they are becoming more popular thanks to their impressive website and daily betting promotions.
  16. 16
    Monster Casino Sports
    Established 2017
    More Details
    Dual Sportsbook & Casino Platform
    10% Cashback on Sports Betting Losses
    'Wager Wars' Leaderboard & Cash Prizes
    Bonus Code
    The code required to claim this sign-up bonus (if any)
    not required
    Live Streaming
    Is there live streaming of sporting events?
    No
    In-Play Betting
    The number of sports with in-play betting available
    30
    Bet Builder
    Can you create your own personalised bets?
    No
    Cash Out
    Can you cash out of bets before an event has finished?
    Yes
    Acca Insurance
    Refund or free bet when one selection in an accumulator lets the bet down
    No
    Monster Casino Sportsbook is the new sports betting offering from this long established casino brand, with a small but select selection of sports to bet on.
  17. 17
    Coral Sports
    Established 2002
    More Details
    One of the UK's Biggest Bookmakers
    Football & Racing 'Super Series' Predictor Games
    'Beaten by a Length' Free Bets
    Bonus Code
    The code required to claim this sign-up bonus (if any)
    not required
    Live Streaming
    Is there live streaming of sporting events?
    No
    In-Play Betting
    The number of sports with in-play betting available
    14
    Bet Builder
    Can you create your own personalised bets?
    No
    Cash Out
    Can you cash out of bets before an event has finished?
    No
    Acca Insurance
    Refund or free bet when one selection in an accumulator lets the bet down
    Yes
    Coral 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.
  18. 18
    BritainBet Sport
    Established 2020
    More Details
    10% Cash-Back on Various Sports
    'Wager Wars' Cash Prizes
    Full & Partial Cash-Out Options
    Bonus Code
    The code required to claim this sign-up bonus (if any)
    BB30
    Live Streaming
    Is there live streaming of sporting events?
    No
    In-Play Betting
    The number of sports with in-play betting available
    16
    Bet Builder
    Can you create your own personalised bets?
    Yes
    Cash Out
    Can you cash out of bets before an event has finished?
    Yes
    Acca Insurance
    Refund or free bet when one selection in an accumulator lets the bet down
    No
    BritainBet is a relatively new sports betting site and casino platform, which offers Bet Builder and Cash-Outs, plus 24/7 customer service.
  19. 20
    William Hill Sports
    Established 2008
    More Details
    'Sports Betting Operator of the Year' 2020 & 2022
    Official Betting Partner of Tottenham Hotspur FC
    Free to Play 'Free or 4' Predictor Game
    Bonus Code
    The code required to claim this sign-up bonus (if any)
    not required
    Live Streaming
    Is there live streaming of sporting events?
    Yes
    In-Play Betting
    The number of sports with in-play betting available
    31
    Bet Builder
    Can you create your own personalised bets?
    Yes
    Cash Out
    Can you cash out of bets before an event has finished?
    Yes
    Acca Insurance
    Refund or free bet when one selection in an accumulator lets the bet down
    Yes
    Named after its founder way back in 1934, William Hill is now one of the world's biggest bookmaker brands and operates over 1400 betting shops throughout the UK.
Show More
Showing 20 of 40
×