FA Cup upsets: greatest shocks in cup’s history, as Grimsby Town beat Southampton to reach 2023 quarter-finals

The beauty of the FA Cup lies in the fact that the small, often non-league sides, come up against the ‘big boys’ of the Premier League and the magic of the tournament occurs when these smaller outfits come out on top. In last night’s (Wednesday 1 March) fifth round fixture between Southampton and Grimsby Town, the FA Cup spark hit again as the League Two outfit beat the Premier League side 2-1.

Grimsby were awarded two penalties either side of half-time and were able to hold on to a historic win which now puts them in the tournament’s quarter-final draw for the first time since 1939. As the problems for Southampton continue to pile one, Harry Haddocks will be on their way down to Brighton and Hove Albion for the quarter-final fixture on Saturday 18 March.

As Grimsby celebrate beating a side which sits 64 places above them in the EFL leagues, here are some of the other biggest upsets in FA Cup history...

2015: Chelsea 2-4 Bradford

Chelsea were top of the Premier League and en route to the title when they took on League One’s Bradford City in the fourth round of the FA Cup. They also looked set to win at least the double as Gary Cahill and Ramires put them 2-0 up at the half-time. However, the final 15 minutes of the match exploded when the former Chelsea youngster Felipe Morais put Bradford level.

Andrew Halliday then made it 3-2 and despite best efforts from Didier Drogba and Kurt Zouma to equalise, John Stead sealed the fourth goal in stoppage time and ended Jose Mourinho’s hopes of FA Cup glory. The League One side went on to beat Sunderland 2-0 in the fifth round before losing to Reading in the quarter-finals.

2011: Stevenage 3-1 Newcastle

Stevenage’s triumph over the Magpies at Broadhall Way in the third round of the FA Cup was only the third time in the tournament’s history that a fourth tier side had beaten a top-flight side in the two decades since the establishment of the Premier League in 1992.

Stacy Long’s defected effort gave Stevenage an early second-half lead and Michael Bostwick then netted a second to put his side in a winning position. Newcastle’s situation deteriorated even further when Cheick Tiote was sent off and despite a long-range goal from Joey Barton, the Magpies were dumped out of the FA Cup competition.

1988: Liverpool 0-1 Wimbledon

In terms of spaces between the two sides, this is not the biggest upset in the FA Cup. However, the result sits high on the list of triumphs in FA Cup folklore. Wimbledon were seventh best in the country at the time and were taking on England’s best.

The Reds played the game ‘the way it should be played’ and collected medals by the bucketful. However a looping header from Lawrie Sanchez gave Wimbledon an unassailable lead and the Dons goalkeeper, Dave Beasant, became the first man to save a penalty at a Wembley FA Cup final when he thwarted an attempt from John Aldridge.

The recently deceased BBC commentator John Motson uttered his infamous line: “The Crazy Gang have beaten the Culture Club.”

1992: Wrexham 2-1 Arsenal

Wrexham were close to having another historic upset this year, but their shining moment came in the 1992 FA Cup when they beat the reigning champions Arsenal in the third round of the FA Cup despite sitting at the bottom of Division Four at the time.

Alan Smith put the Gunners in front and they looked to be headed for glory until Mickey Thomas put home a superb free-kick 10 minutes from the final whistle. Steve Watkin then netted a last-minute winner and George Graham’s men suffered utter humiliation.

1972: Hereford United 2-1 Newcastle

This is arguably the most historic win in FA Cup history. The Southern League side went to great lengths to secure a 2-2 draw at St James’ Park and the return match was postponed three times due to inclement weather. On a mudbath of a pitch, the Magpies thought they would come away unscathed as Malcolm Macdonald headed an 82nd-minute goal.

However, Hereford’s Ronnie Radford then produced one of the most famous FA Cup goals ever to put his side equal with Newcastle and a huge pitch invasion soon followed. Ricky George then expertly scored an extra-time winner and Hereford would go down in history as the side which produced one of the greatest FA Cup fixtures of all time.