There’s a sense among the proletariat that soccer’s elite are attempting to sap away the very essence of what makes the sport so special.

It’s soccer’s unpredictability that renders it so endearing, yet the ambitions of those at the top to remain a part of an untouchable bracket seemingly contradicts the ideal of variance.

And while Europe’s leading divisions and UEFA’s premier club competition are won by so few in modern times, there‘s still scope for unpredictability to be enjoyed and savored. The domestic cup competitions offer a nostalgic throwback to simpler times, when everything was supposedly just that little better.

In England, it’s the FA Cup that’s been bestowed with “magic” for generations, yet there‘s been ample proof over the years that it’s less esteemed younger brother was blessed with some fairy dust, too.

We could take you back through the annals of history, to the very start of the League Cup’s inception, when Swindon Town beat Arsenal in the 1969 final and fourth-tier Chester stunned reigning English champions Leeds United five years later. However, for this ranking, we‘ve kept it more modern, using the Premier League’s birth (August 1992) as our starting point.

Here are seven of the biggest League Cup upsets, ranked by the difference in league position when the two teams met.

7. MK Dons 4–0 Man Utd (Aug. 26, 2014)—34 Places

As we’ll learn, Manchester United and the League Cup second round just don’t mix.

At the start of the 2014–15 campaign, the Red Devils visited Stadium MK for their first second-round tie in 19 years. Louis van Gaal was the man at the helm, and the start to his rather indifferent tenure in Manchester was dire.

This was the nadir, though: losing 4–0 away from home against League One opposition. Man Utd couldn’t contain Will Grigg or Benik Afobe, and a future star came to the fore in Dele Alli, who’d join Tottenham Hotspur the following year.

But hey, it wasn’t all bad for supporters, given that the club had announced the arrival of Ángel Di María from Real Madrid that same evening.

6. Grimsby 2–2 (12–11p) Man Utd (Aug. 27, 2025)—56 Places

Man Utd’s next second-round venture, almost 11 years to the day they’d much rather have succumbed to Milton Keynes’s curious number of roundabouts on their way to Stadium MK, saw them travel to Cleethorpes and face a Grimsby Town team enjoying themselves toward the League Two summit.

Unlike Van Gaal, Ruben Amorim had already settled into his role at Old Trafford, and supporters backed the Portuguese to turn things around after a dismal 2024–25 campaign ended with defeat to Tottenham Hotspur in the Europa League final.

United spent the summer retooling a previously lifeless attack, and there were starts for two of them—Matheus Cunha and Benjamin Šeško—here. They lasted the duration, joined by fellow newbie Bryan Mbeumo for the second half.

United were 2–0 down when Mbeumo entered the fray, and it was the Cameroonian who ignited the visitors’ revival. Harry Maguire’s 89th-minute equalizer took the tie to penalties, and after a lengthy shootout, Mbeumo’s saved spot-kick on the second go-around proved decisive.

5. Bradford 1–1 (3–2p) Arsenal (Dec. 11, 2012)—65 Places

Arsenal’s issues from 12 yards certainly predate 2026.

Entering the 2012–13 season, the Gunners had gone seven years without a trophy. They were perennial title contenders in preseason, but supporters just wanted a cup to celebrate, to get the ball rolling again.

The League Cup was thus significant, and Arsenal had seemingly been gifted a route into the semifinals when they were paired against League Two Bradford City in the last eight.

However, it proved to be a troublesome evening for Arséne Wenger’s side, even if it seemed that captain Thomas Vermaelen had rescued them from the brink with two minutes to play. The Belgian had merely canceled out Garry Thompson’s volleyed opener, and his night wasn’t over.

A tense shootout at the Coral Windows Stadium was decided by Vermaelen, who followed Santi Cazorla and Marouane Chamakh’s lead by missing from 12 yards. The defender’s mishap was the decisive blow, as the Bantams celebrated a memorable victory and eventually made their way to the final by beating Aston Villa over two legs.

We don’t need to discuss what happened at Wembley.

4. Man Utd 0–3 York (Sep. 20, 1995)—65 Places

The biggest second-round upset in the competition’s history of course features Man Utd, which arrived soon after Alan Hansen famously quipped the Red Devils couldn’t “win anything with kids” following their opening-day defeat at Aston Villa.

United recovered well, though, and were expected to have no issues over two legs against a York City team that was struggling in the third tier. They’d won just two of their opening 10 outings of the season ahead of the first leg.

Sir Alex Ferguson refused to rotate drastically for York’s visit, yet his team was stunned by a Paul Barnes (father of Newcastle United winger Harvey) brace and eventually lost 3–0.

Their rally didn’t arrive until the return leg, when they were inspired by the return of Eric Cantona from a nine-month ban. Scott Jordan’s strike was enough for the underdogs, who advanced as 4–3 aggregate winners.

3. Liverpool 2–2 (2–4p) Northampton (Sep. 22, 2010)—69 Places

This was a pretty wretched Liverpool team, it must be said. The doldrums.

Still, almost 70 places in the English soccer pyramid separated the Reds and League Two side Northampton Town when they met in the third round toward the start of Roy Hodgson’s miserable reign at Anfield.

Liverpool’s goalscorers on the day, Milan Jovanović and David Ngog, typified just how bleak things were for the Merseysiders at the time.

Ngog’s extra time header forced the tie to penalties, but the French forward was one of two to miss from the spot for the Reds, allowing the visitors, 17th in the fourth-tier at the time, to advance.

2. Colchester 0–0 (4–3p) Tottenham (Sep. 24, 2019)—71 Places

Mauricio Pochettino had warned Tottenham supporters about the “painful rebuild” that lay ahead before Lucas Moura’s improbable hat trick in Amsterdam sent the Lilywhites into the 2019 Champions League final.

However, even the pessimistic Argentine wouldn’t have thought his side would slump as miserably as they did on a mild Essex night in late September.

Colchester United were the lowest-ranked team left in the competition when the Champions League finalists rocked up for a third-round tie. The Lilywhites were utterly lifeless, seemingly bereft of hope.

The hosts appeared unshackled, able to take the game to a shootout with relative ease. Given how the evening had unfolded, there was only going to be one winner. Christian Eriksen and Moura were denied, and although Jevani Brown’s ‘Panenka’ didn’t quite come off, that proved to be the hosts’ only blemish from 12 yards.

Pochettino left his post six weeks later.

1. Fleetwood 1–1 (5–3p) Arsenal (Oct. 27, 2026)—84 Places

That’s right, it’s the biggest upset in League Cup history.

Plenty wouldn’t have even tuned in to Arsenal’s trip to Fleetwood Town at the start of the fourth round, expecting a rather dull procession.

However, the Premier League champions, ruffled by the remnants of a storm, found themselves with work to do when on-loan Fulham striker Aaron Loupalo-Bi outwitted youngster Marli Salmon and converted beyond Illan Meslier midway through the first half.

Viktor Gyökeres, who toiled for much of the night without reward, drew Arsenal level after the restart, but a young Fleetwood outfit remained dogged and resolute in the aftermath. They resisted Arsenal’s sustained pressure and worked tirelessly to reduce the tie to a lottery.

The Gunners initially matched Fleetwood’s precision from 12 yards, until Bruno Guimarães had his telegraphed effort saved by Jay Lynch. The hosts had match point, and 19-year-old Conor Haughey dispatched his spot kick as if he was enjoying a kick-about with his pals.