Exeter, Devon UK • Jul 18, 2024 • VOL XII

Exeter, Devon UK • [date-today] • VOL XII
Home Sport Five of the Best: League Cup Giant Killings

Five of the Best: League Cup Giant Killings

Ahead of this week's fourth-round Carabao Cup ties, Joshua Hull goes back in time to review some of the competition's biggest upsets and exits of all time.
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Image: Paul/VegasEddie

Ahead of next week’s fourth-round Carabao Cup ties, Joshua Hull goes back in time to review some of the competition’s biggest upsets and exits of all time.

The League Cup, at least in the current footballing climate, has become something of an oddity; many supporters count the competition low on their list of priorities, some have even become agnostic when faced with the idea of winning it.

Managers are not exactly enamoured by these cup ties either, constantly trotting out second-string line-ups and treating serious, competitive fixtures with the contempt of a reserve match. Trivial naming right changes aside, the animosity appears to stem from the idea that the cup is unrivalled in terms of allure and magic when compared with its counterpart, the FA Cup.

The scenes at the JobServe Community Stadium in round three last month – Colchester United of League Two beating Champions League finalists Tottenham on penalties – proves this is merely a myth. Delve further into the record books and you’ll find that surprise exits for England’s elite, top-flight outfits have, in fact, been a regular occurrence in the competition’s 59-year history.

So, with all said and done, here’s our run-down of five of the most memorable upsets.

Bradford 1 – 1 Arsenal (3-2 pens), 2012

Arsene Wenger’s Arsenal were not the invincible, world-class laden side they used to be. However, they travelled to Valley Parade with a chance to progress into the semi-finals of the competition and edge closer to ending their seven-year stint without a trophy. After all, their Premier League superiority and the international talent of Santi Cazorla, Lukas Podolski, among others, would surely be enough to see off a Bradford City team who were 4th in League Two and cost barely a penny to assemble. But what the hosts lacked in big-money superstars, they more than made up for with their organisation, discipline, and incredible team spirit.


Phil Parkinson’s troops led from the 16th minute through Gary Thompson’s goal, right up until the 87th when Thomas Vermaelen pinched an equaliser. There was always a sense that the Gunners were in danger, the weight of expectation just too much for this group. As the contest went to penalties, that feeling grew. Cazorla, Marouane Chamakh, and Vermaelen failed to convert from the spot and Bradford were granted a famous night for the history books – as well as a fully deserved semi-final place.

Manchester United 0 – 3 York, 1995

The 95/96 season was a significant one for Manchester United and Alex Ferguson. Despite Blackburn beating them to the Premier League title in the previous year, the Red Devils decided against making a major summer signing, instead opting to draft in youngsters such as David Beckham, Paul Scholes, and Gary Neville – members of the now-fabled ‘Class of 92’. With the experienced trio of Paul Ince, Andrei Kanchelskis, and Mark Hughes all having recently moved on, this was seen as a major risk. And, following a dismal 3-1 defeat to Aston Villa in the August, Match of the Day pundit Alan Hansen infamously claimed, “You can’t win anything with kids”. Ferguson appeared to have made a mistake.

It is often forgotten that those United starlets suffered an even more embarrassing result a month later when York City, then a League One outfit, went to Old Trafford and eased to a 3-0 victory in the second round of the cup. In those days, ties were played over two legs and even though United managed a 3-1 win away from home, the Minsterman claimed a famous scalp with a 4-3 aggregate success. Man Utd’s season would turn out rather well in the end though, as they went on to earn the league and FA Cup double. Though Hansen’s words were seen as the main motivational tool, this humbling defeat to lower league opposition was just as important a lesson for Becks and company.

Southend 1 – 0 Manchester United, 2006

Fast-forward nearly eleven years and the red side of Manchester were involved in another League Cup surprise. Championship strugglers Southend dished out the fourth round defeat, remarkably, in a season which would see them relegated – still yet to return to that level. Ferguson’s United, on the other hand, were top of the Premier League table and would remain there at the season’s conclusion. Even with the disparity between the two teams’ league position, the Red Devils included international icons Cristiano Ronaldo and Wayne Rooney in their line-up to prevent a cup exit.


Both players could only watch and admire, however, as Freddy Eastwood’s 30-yard rasping free-kick struck the net in the first half. And though later on their influence grew, Shrimpers goalkeeper Darryl Flahavan was on hand to deny them with several excellent saves, each time sending the majority of Roots Hall into raptures. The celebrations at full-time were even louder as Southend held on to their single goal lead, reaching the quarter-finals of the cup and dumping out the holders in the process.

Liverpool 2 – 2 Northampton (2-4 pens), 2010

Mention the name Roy Hodgson to a Liverpool supporter and you will likely receive a rather disgruntled response. His lacklustre transfer recruitment, the team’s atrocious Premier League record, and a sterile, defensive style of football are all major factors as to why he is so unfavourably thought of by Scousers and only lasted six-months in the Anfield hot seat. Hodgson was also responsible, at least partially, for one of the worst results in the club’s long and illustrious history when they were beaten by League Two Northampton Town.

Milan Jovanovic’s goal after nine minutes got the Reds off to a strong start in the third round fixture, but that was honestly about as bright as it got. Billy McKay’s close-range finish for the Cobblers took the game to extra time, where Michael Jacobs then put the rank outsiders in front. David N’Gog rescued penalties for the hosts with a header in the 116th minute, however, he was one of those who missed from the spot under pressure. Eventually, the responsibility fell to Ghanaian midfielder Abdul Osman to slot home his kick and give lowly Northampton an evening to remember for the rest of their lives.

MK Dons 4 – 0 Manchester United, 2014

Apologies to United fans because, yes, you’ve made the list again. The other two results are mainly noticeable for the period in which they are set in: during Sir Alex’s all-conquering reign, a time where they had become so difficult to beat. This match, at the start of Louis van Gaal’s ultimately underwhelming era, is included simply due to the sheer one-sidedness of the scoreline. Truthfully, the Reds were an entirely different entity to that of before, no longer feared and no longer mighty. Winless in his first two league games, a second-round trip to MK Dons should have been a way to kick-start van Gaal’s reign. Instead, it was a setback of disastrous proportions.

Doubt had already crept in before kick-off at Stadium MK as United named a severely weakened starting eleven. Of those players, Saidy Janko, Reece James, and Marnick Vermijl would barely last another year at Old Trafford. However, a 4-0 battering was a stretch way beyond the imaginable. Will Grigg and Benike Afobe both hit a brace for the League One team, while an 18-year old Dele Alli pulled the strings in midfield. A masterful performance from Karl Robinson’s side, one that holds up as Milton Keynes’ greatest ever in their short fifteen-year history as a football club.

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