FA Cup Betting: Analyzing the biggest potential upsets of the Third Round

The FA Cup is back, and the magic of this tournament sparks back into life. The third round is when the Premier League teams enter the fray, and that is when we are most likely to get a huge upset, as the topflight teams are caught by surprise by their lower league opponents.

We’ve taken the four biggest outsiders this weekend and looked at their chances of an upset.

Chelsea vs. Chesterfield

At +3800, Chesterfield are the biggest underdogs on the entire FA Cup slate this weekend. It's not normally the odds you expect to see on a team currently on a 14-game unbeaten streak, but that’s the reality when Chesterfield head to Stamford Bridge to face Chelsea.

Chelsea are second  in the Premier League, while Chesterfield top the National League — England’s fifth tier of football. There are a total of 91 points that separate the two teams, and that gulf in class is unfortunately going to likely be too much for James Rowe’s side.

The Premier League side aren’t in particularly good form, having dropped points to Everton, Wolves, and Brighton in the league in December, but they battled back to earn a 2-2 draw with Liverpool last week and comfortably beat Tottenham 2-0 on Wednesday, so they are somewhat back on track.

Thomas Tuchel’s men have lost just one of the last 22 games, and while he’s likely to give plenty of his superstars a rest this weekend, they should still be too strong.

Upset verdict?

Even with a second-string Chelsea side out on the field, they should be too good for non-league Chesterfield.

Prediction: Chelsea 3-0 Chesterfield (+540)

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Tottenham vs. Morecambe

League One Morecambe will also make the trip to London, where they’ll face Antonio Conte’s Tottenham. Spurs were well beaten by rivals Chelsea in the League Cup this week, but that game aside, Tottenham had been in good form. Since taking over, Conte has not lost a league game and picked up 17 points from a possible 21.

Morecambe, meanwhile, are in deep trouble in League One and find themselves just five points clear of the relegation zone. Their league record since the start of October reads 2-9-3, and they’ve conceded more goals in the division than any other team (2.04 a game on average).

Conte will likely rest Harry Kane, Heung-Min Son, and others, but this is still a competition Spurs will target as they attempt to end a 14-year trophy drought.

Morecambe would no doubt prefer to put their focus on staying in League One, so this one could turn ugly quickly for the visitors.

Upset verdict?

If Morecambe are conceding more than two goals a game in League One this season, it’s frightening to think what Tottenham could do to them, even without Kane.

Prediction: Tottenham 5-0 Morecambe (+900)

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Newcastle vs. Cambridge United

Like Morecambe, Cambridge United are struggling in League One, although they are up in 16th and are a far comfier nine points clear of the relegation zone. This weekend, they have the chance to visit the richest club in world football, Newcastle United.

The Magpies put up their best performance of the season in their last match, as they held Manchester United to a 1-1 draw, and arguably deserved all three points. However, that shouldn’t take away from the fact that this Newcastle team have won just one of 20 games in all competitions this season and are 19th in the Premier League.

Newcastle fans have been shocked in the cup recently before, crashing out 3-0 to League One Oxford United in 2017, at a time when Newcastle had won 14 of their 18 league games and were on their way to being promoted back to the Premier League.

They’re in far worse form now and while Cambridge haven’t scored for three games, they will be more than fired up for this one.

Upset verdict?

Newcastle looked to be turning a corner against Manchester United, but this game is a potential banana skin, and Eddie Howe’s focus must be on Premier League survival. Cambridge can do enough to earn a shock replay.

Prediction: Newcastle 1-1 Cambridge United (+900)

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Liverpool vs. Shrewsbury Town

Liverpool come into this game with all sorts of problems, thanks to a combination of international call-ups, injuries, and now an outbreak of COVID-19.

A significant number of players and staff, including coach Jurgen Klopp, were reported to have tested positive this week. While there is no clarity on who or how many there were in total, it was significant enough that the training centre was shut down from Wednesday, and their game against Arsenal in midweek was postponed.

The announcement earlier this week was that this match will go ahead, but Liverpool will be forced to field a young, inexperienced squad — and that may open the door for League One Shrewsbury.

The Shrews will smell an upset at Anfield and will no doubt be chomping at the bit to take on a Premier League giant. They’re unbeaten in four games in League One, which will give them a confidence boost and can feed off the memories of January 2020.

That year in the FA Cup, they came back from 2-0 down to draw 2-2 with Liverpool, who were in the process of running away with the Premier League title. A slightly out-of-sorts Liverpool could present the opportunity for another famous Shrews result.

Upset verdict?

No matter how young the side, Liverpool always have goals in them, while Shrewsbury Town are dangerous enough on the break to trouble the hosts. The Shrews will fear nothing and can grab a famous result at Anfield.

Prediction: Liverpool 2-2 Shrewsbury Town (+1800)