FA Cup Betting Tips

Wembley StadiumThe FA Cup is the biggest club cup competition in England and is not only popular at home but watched my millions of football fans overseas each year.

The reason for this popularity is that not only is it the oldest competition of its type in the world, it also gives teams from as low as the tenth tier the chance to take on the biggest clubs in the country.

Here we’ll provide the best betting options from each round, all the way from the first round proper in November to the Wembley final in May.

FA Cup Matches – 8th to 11th November 2019

Date Time Channel Match Tip
08/11/19 19:55 BBC Two Dulwich v Carlisle Carlisle Win
09/11/19 13:00 N/A Sunderland v Gillingham Sunderland Win
09/11/19 15:00 N/A Bolton v Plymouth Bolton Win
09/11/19 15:00 N/A Ipswich v Lincoln Ipswich to Win -2
10/11/19 12:00 BT Sport Dover v Southend Southend Win
10/11/19 14:15 BT Sport Hayes v Oxford Oxford to Win -1
11/11/19 19:45 BT Sport Harrogate v Portsmouth Portsmouth to Win -1

The first round of the Emirates FA Cup takes place this weekend, with clubs from Football League’s One and Two joining the competition and that we means we have some truly huge clubs entering the fray, including a number of former winners. We have several tasty ties to look forward to, starting with Friday night’s clash between Dulwich Hamlet and Carlisle United.

2008 FA Cup winners Portsmouth are in first round action on Monday evening, as Kenny Jackett’s men look to avoid an upset when they take on Harrogate Town of the National League at Wetherby Road. What will unfold in the first round of this famous competition over the course of the weekend and will we get the usual stories of plumbers beating pros?

Carlisle to Edge Out Dulwich

On Friday night, Gavin Rose’s Dulwich entertain Steven Pressley’s Carlisle at Champion Hill in London. The Hamlet are struggling in the National League South at the moment, while the Cumbrians are hardly flying themselves, down in 19th in EFL League Two.

Dulwich have been in poor form of late, failing to win in league action since August. Rose’s side sit 16th in the National League South table at the moment, just three points off the drop. However, they did beat Havant & Waterlooville 2-1 away from home in the previous round of the FA Cup.

League Two Carlisle head to Champion Hill unbeaten in their last two league games. After drawing at Leyton Orient, the Blues picked up a much-needed 2-1 victory over Macclesfield Town at Brunton Park last time out and they appear to be moving in the eight direction.

With Dulwich in such poor form, Carlisle’s experience and class should get them over the line in the capital on Friday. Back the visitors to prevail at 8/11.

Tough Test for Campbell’s Shrimpers

Dover Athletic Crabble Stadium

By ChrisTheDude, Wikimedia Commons

Southend United have been in abysmal form in EFL League One so far this season, losing 14 of 17 league games. With that in mind, a trip to Dover Athletic of the National League in the cup is something that Sol Campbell and his side could do without right now.

Andy Hessenthaler’s troops are doing okay in the National League at present, picking up eight wins from 19 matches to sit in 12th spot. Dover beat Weymouth 2-1 on the road in the last round of the cup and will be eyeing up that third round glamour tie.

In contrast, Southend have very much had a season to forget so far. The Shrimpers go into this one having lost eight of their last nine in all competitions. The Essex club recently appointed former England defender Campbell, but United have lost all three games under his guidance so far, conceding eight goals along the way. Much as Campbell likes to talk the talk, thus far his managerial career, albeit a short one, has not been anything to get excited about.

Southend have not won in any competition since beating MK Dons away from home in League One back in September. This will no doubt be a stern test for the third tier strugglers, but we fancy Campbell’s men to sneak a win (13/10) at the Crabble Athletic Ground this weekend.

Comfortable Win for Pompey

Portsmouth Fratton Park

By Ben Hardinge, flickr

Kenny Jackett takes his Portsmouth side to North Yorkshire on Monday night to face Simon Weaver’s Harrogate Town at Wetherby Road. League One Pompey are the odds-on favourites in this one and know that if they match the hosts for effort they should prevail.

Harrogate, who missed out on promotion to the Football League in the play-offs last term, are sitting nicely in seventh place in the National League at the moment. Town have been hard to beat, with only leaders Bromley losing fewer games up until now.

Portsmouth, who thumped Southend in the league on Tuesday, have lost just one of their last nine league and cup encounters. Jackett’s boys are one of the favourites for promotion from League One this term, but they are down in 13th at the moment.

Portsmouth, who lifted the FA Cup under Harry Redknapp in 2008, will fancy their chances of getting the better of their National League opponents on Monday and we do too. Put some money on the away team to win -1 at 7/5.

  • Sunderland v Gillingham - Phil Parkinson’s Sunderland, who won this famous trophy in 1973 and 1937, and Steve Evans’ Gillingham meet in an all-League One FA Cup affair on Saturday. The Black Cats have won only one of their last four in all competitions, but the Gills have lost five of their past nine. Sunderland should edge this one (4/7) at the Stadium of Light.
  • Bolton v Plymouth - League One’s bottom club Bolton Wanderers have won the FA Cup four times, most recently in 1958. It’s been a tough time for them of late but they have won their last three and welcome League Two outfit Plymouth Argyle to the University of Bolton Stadium on Saturday. Things are slowly but surely starting to click into gear for Keith Hill’s men, and we’re backing the Trotters to claim a fourth win on the spin at the weekend. The Wanderers victory is very nicely priced at odds of 31/20.
  • Ipswich v Lincoln - High flying Ipswich Town entertain Lincoln City at Portman Road in the first round of the FA Cup on Saturday. Promotion will be Town’s main aim this season, but the Tractor Boys should ease past the struggling Imps in the cup at the weekend. Have a punt on Ipswich to win -2 at 11/2.
  • Hayes v Oxford - BetVictor Southern League Premier side Hayes & Yeading United play Oxford United of League One on Sunday. Karl Robinson’s boys are a team in superb form, and the League One outfit should have no problems in this cup tie. Oxford are available at 4/6 to win -1 and that’s the call for us here.

FA Cup Betting Strategy

The oldest national football tournament in the world, and certainly the most famous, the FA Cup holds a special place in the hearts of football fans around the globe. Life has changed a good deal since Wanderers beat Royal Engineers in the first FA Cup final at the Kennington Oval way back in 1872, but this footballing institution has remained a relative constant and has brought joy (and heartache) to millions over the years.

In the modern era of big money transfers and astronomical broadcasting rights deals, there is something romantic about the FA Cup, or The Football Association Challenge Cup, as it is officially known. Any competition in which Exeter City can earn a replay against then FA Cup holders Manchester United, or in which Shrewsbury can beat Everton or Hereford get the better of Newcastle, is a competition that is sure to capture the imagination.

Here we bring you details of some of the biggest FA “Cupsets” of all time, as well as outlining betting strategies you can employ to help you win money when having a punt on the FA Cup. We’ve also got a brief history of the competition and a list of winners – some you might never have heard of!

Seeking Value Bets

As we have mentioned elsewhere on the site, an effective betting strategy is one which focuses on “value”, that is, seeking out bets for which the odds give you the edge over the bookmaker, rather than the other way round.

This occurs when the odds offered on a given outcome imply a probability that is less than the actual probability of that outcome occurring. In reality, calculating the actual probability of any given event occurring in sport is far from an exact science given the number of variables. The easy availability of masses of information relating to, for instance, an FA Cup match between Arsenal and Liverpool, means it is very likely that the odds the bookmakers offer will reflect the actual probabilities involved, plus a little built in for their profit margin of course.

Information relating to any given football match could be things like the weather conditions, injury news, historical statistics, current form of players or teams involved, whether the manager had a row with his wife on the morning of the game, whether the star striker ate a dodgy omelette the night before the game, and more or less anything else you could think of.

It stands to reason that when the biggest sides in the land are playing, much of the information relating to the game will be in the public domain, and hence will be taken into account by the bookies when they set the odds. It is also the case that, unless you have very good connections to someone who works for one of the clubs involved, the bookies are going to get hold of any pertinent information before you are. Be that about, for instance, a player getting a late injury or there being a training ground bust-up, or indeed anything else.

This is less likely to be the case, however, when it comes to matches involving teams much lower down the pecking order. For example, if Fleetwood play Alfreton or Hitchin Town play Solihull Moors in the FA Cup First Round (as they did in the 2018-19 season), there is every possibility that local fans will know more about their side’s chances of success or about any late injury scares or how the players are form-wise than the bookies will. Therefore there could be a good chance to seek out a value bet based on superior information.

Can You Find The Cupsets?

There have been some almighty mismatches in the FA Cup over the years, but – as we detail below – there have been a good number of giant killings too. And identifying a match in which a long odds underdog might just prevail against a bigger and (on paper) much better side can pay handsome dividends.

Identifying such giant-killing opportunities could be seen to be as much an art as a science as it is often the case that a side who pulls off a shock result has had to ride their luck for large chunks of the game in question. But sometimes the stars align and the magic of the FA Cup produces the kind of results that excite the neutral and, especially, those who’ve backed the underdog!

Factors that have at least contributed to top sides getting booted out of the FA Cup include the following:

  • Complacency – Big name footballers and even managers can fall foul of their egos on occasion, and taking the opposition too lightly has been the demise of many a side in this competition. How often have managers of Premier League sides decided to play an underprepared second string against lower league opposition in order to rest their stars, only for the game to be drawn and another fixture be added to the schedule!
  • Conditions – Churned up, sloping pitches, changing rooms that make your average 1980s swimming baths look plush, freak hurricane/blizzard/monsoon weather… any and all of these factors can serve to fill visiting players and staff from the odds-on favourite with anxiety, while at the same time bolstering the underdogs who start to think it might just be “our day”.
  • Form – It has often been the case that a team flying high towards the top of the Championship, or even League One, has been more than a match for a side from the Premier League who is in a terrible run of form. The confidence built up by a winning run can often give a lower league side the edge against a side from a division or two above who has been struggling for form.
  • Cup Specialists – Some teams and even managers have built up a reputation as “Cup Specialists”. From a managerial perspective these often come in the form of master motivators like Martin O’Neill or Ron Atkinson, while some teams just seem to drift through to the latter stages of the FA Cup year after year without too much bother, Arsenal being a prime example.

Tournament Structure

The FA Cup starts for many football fans at the First Round stage, and still others when the “big boys” are introduced at the Third Round stage. But in reality there has been a whole lot of football played before the Competition Proper.

Each season the FA Cup actually gets underway in August when the Qualifying Competition begins with the 184 matches of the Extra-Preliminary Round. This is the stage at which dreams are created amongst the lowest of branches of the English footballing tree; that is those in Level 9 and 10. These levels feature teams who ply their trade in such divisions as the Hellenic League Division One West and the Spartan South Midlands League Division One.

The Preliminary Round of the Qualifying Competition then sees the inclusion of teams from Level 8 (such as those playing in the Northern Premier League Division One East) for a total of 160 matches, with the Qualifying Competition continuing with Level 7 clubs added for the First Round (116 matches), Level 6 clubs for the Second Round (80 matches), none added for the Third Round (40 matches) and Level 5 clubs joining the fun at the Fourth Round stage of 32 matches (that is, those sides from the National League, the highest non-league division).

The Qualifying Competition gets sewn up in October each season, and the Competition Proper gets going in November when the First Round sees the introduction of Level 3 and 4 clubs, that is those playing in EFL League One and EFL League Two. There are 40 matches played in the first round.

The Second Round sees no additional teams, so there are 20 matches at this stage, before the round every non-league and lower league side wants to reach: the Third Round. This is where that money-spinning trip to Old Trafford or that giant-killing opportunity can materialise for the minnows as the sides from the Championship and the Premier League get involved. With 32 matches in the Third Round, it’s a straight knockout from here on in with no more teams entering the competition.

As such, the Fourth Round sees 16 matches, the Fifth Round, sometimes called the last 16, eight matches, the Quarter-Finals (as the name suggests) has four matches, the Semi-Finals two matches and the Final, of course, is just a single match. The Semi-Finals and Final are played at Wembley Stadium.

Note that during the Qualifying Competition, sides are drawn against rivals from similar geographical regions to ensure the smallest clubs don’t incur too much in the way of travel costs. If sides draw a match after normal time, the match goes to a replay at the ground of the away side, at least until the Fifth Round proper.

If the replay is also a draw after normal time, the match goes to extra time and then, if required, a penalty shootout. Matches from the Quarter-Finals onwards do not go to replays. If the match is level after normal time, it goes straight to extra time and then, if needed, a penalty shootout.

The winners of the FA Cup currently qualify for the following season’s UEFA Europa League and this is the case whether the winning side is in the Premier League or not. If however, the FA Cup winner qualifies for the Champions League, that takes precedence. In the past the losing FA Cup finalist would take the Europa League place, but from the 2015-16 season that place goes instead to the highest placed Premier League side who has not already qualified for Europe.

A brief history of the FA Cup

The first FA Cup, as mentioned, took place in the 1871-72 season after Charles W. Alcock had proposed the formation of the tournament to the committee of the Football Association on 20th July 1871.

The tournament started on 11th November 1871 when seven matches were scheduled to take place. Only five games were actually played though as the opponents of both Royal Engineers and Wanderers (the eventual finalists) both withdrew from the competition. The first FA Cup final took place on 16th March 1872 at the Kennington Oval, Wanderers beating Royal Engineers 1-0 thanks to a 15th minute goal from Morton Betts.

Fear not, we’re not going to go into quite so much detail for every year’s FA Cup competition from then to the present, but there are a few things worth noting from the history of this prestigious tournament. Here are some of the more interesting developments and occurrences over the years:

  • 1871-72 – First FA Cup took place.
  • 1888-89 – Qualifying rounds were introduced; Warwick County became the first non-league side to perform a giant killing when they beat First Division Stoke 2-1 away on 6th October 1888.
  • 1900-01 – Tottenham Hotspur became the first (and only) non-league club to win the FA Cup since the formation of the Football League in 1888. Tottenham plied their trade in the Southern League at the time.
  • 1922-23 – For the first final at Wembley Stadium, known at the time as the Empire Stadium, more than 200,000 fans watched Bolton Wanderers get the better of West Ham 2-0.
  • 1925-26 – Teams from the top two divisions entered at the Third Round stage of the FA Cup for the first time.
  • 1966-67 – Substitutes were permitted for the first time.
  • 1969-70 – The 1970 final between Chelsea and Leeds United was the first to go to a replay which was played at Old Trafford.
  • 1990-91 – Fourth round tie between Arsenal and Leeds United ended 0-0 and went to a replay… which ended 1-1 and went to a second replay… which ended 0-0 to take it to a third replay, which Arsenal won 2-1. After this the rules were changed so that games level after normal time of a replay would go to extra time and then penalties if needed.
  • 1991-92 – First penalty shootout in the FA Cup when Rotherham beat Scunthorpe 7-6 on pens in their First Round replay.
  • 2000-01 – Replays no longer played in Semi-Finals and Finals
  • 2001-06 – FA Cup Finals played outside England for the first time. As Wembley Stadium was undergoing redevelopment, the finals during this period were played at the Millennium Stadium in Cardiff, Wales.
  • 2016-17 – Replays abolished for Quarter-Finals.

Which Teams Have Won the FA Cup?

At the time of writing (prior to the 2019 final), Arsenal hold the record for winning the most FA Cups with 13 in total. Manchester United are hot on their heels with 12, while Chelsea and Tottenham have landed eight and eight, Liverpool and Aston Villa have earned seven apiece.

As mentioned, Wanderers – an amateur club based in London who started life in 1859 as Forest Football Club – won the first FA Cup final in 1872. They went on to win the cup five times before it was dissolved in 1887.

The other two sides who are no longer in existence but who won the FA Cup are Clapham Rovers (1880) and Blackburn Olympic (1883). Others who are not exactly household names who have won the cup and are still plying their trade include: Old Carthusians (1881 – former pupils of Charterhouse School), Royal Engineers (1875 – an army side representing the Corps of Royal Engineers).

Top 10 FA Cup Giant Killings

  1. Wrexham 2-1 Arsenal (1992) – George Graham’s Arsenal were just not at the races at the Racecourse Ground in Wrexham as they went down 2-1 to relative minnows Wrexham. The Gunners made up for it the following year when they won the FA Cup.
  2. Shrewsbury 2-1 Everton (2003) – Shrewsbury boss Kevin Ratcliffe relished the chance to play his old club in the FA Cup, and he made the most of the occasion by leading his side to victory. There were 80 league places between the teams at the time, but you wouldn’t know it looking at the poor performance from David Moyes’ men.
  3. Sunderland 1-0 Leeds United (1973) – Don Revie’s Leeds United were at the height of their powers in 1973, but that didn’t stop Bob Stokoe’s determined Black Cats battling to a 1-0 win at Wembley in the 1973 final.
  4. Wimbledon 1-0 Liverpool (1988) – Ahead of the 1988 FA Cup final everything pointed towards a Liverpool victory. Kenny Dalglish’s side of stars had just been crowned league champions and Bobby Gould’s “Crazy Gang” were widely expected to take a real beating in the final. Lawrie Sanchez got the winner for Wimbledon with a looping header and one of the biggest FA Cup final upsets came to pass.
  5. Sutton United 2-1 Coventry City (1989) – Non-league Sutton got the better of top flight Coventry in 1989, which is notable enough, but add in the fact that Coventry had won the FA Cup just 19 months earlier and it makes this one of the great FA Cup giant killings.
  6. Wigan Athletic 1-0 Manchester City (2013) – Roberto Martinez’s Wigan had always been easy on the eye, but given that they had struggled all season no one really thought they stood a chance against Man City in the Final. The doubters were wrong though as Wigan won the game 1-0… and then got relegated from the Premier League.
  7. Chelsea 2-4 Bradford City (2015) – League One side Bradford not only beat then Premier League leaders Chelsea in this FA Cup match in 2015, they did it at Stamford Bridge. Not even Didier Drogba playing the whole match or Eden Hazard, Willian and Cesc Fabregas coming off the bench could save the Blues’ blushes.
  8. Stevenage 3-1 Newcastle (2011) – League Two side Stevenage fully deserved their victory against Premier League side Newcastle, who had the likes of Joey Barton and Kevin Nolan in their starting line-up.
  9. Yeovil Town 2-1 Sunderland (1949) – this Fourth Round tie resulted in one of the few FA Cup triumphs for a non-league side over one from the top division.
  10. Hereford United 2-1 (aet) Newcastle United (1972) – This FA Cup Third Round replay was a heroic extra time triumph for Hereford, who were playing in the Southern Football League, a long way below First Division Newcastle.