Starting life in 1960, The English League Cup pitted professional teams from within the English football pyramid against each other in a knock out style tournament. Under it’s various guises due to sponsorship over the years, the League Cup will be remembered as the Milk Cup for those in the 80’s, Littlewoods Challenge Cup, Rumbelows Cup, Coca-Cola Cup, Worthington Cup for those in the 90’s, Carling Cup, Capital One Cup in the 00’s and the Carabao Cup since 2017.

Over it’s 60 year history, the League Cup has staged some of football’s biggest upsets and shock results, where lower league clubs have toppled their larger counterparts. Here, we take a look at ten of the most shocking moments in League Cup history.
1. Bradford City’s Fairytale Run (2012-13)
One of the most memorable runs in recent League Cup history is that of Bradford City in the 2012-13 season. Phil Parkinson’s fourth-tier side defeated Premier League clubs Wigan Athletic, Arsenal, and Aston Villa to reach the final. Though they were beaten by Swansea City in the final, their journey remains a quintessential example of a ‘giant-killing’ run. The stuff that dreams are made of!

2. Northampton Town vs Liverpool (2010-11)
Northampton Town, a club from the fourth tier of English football, ousted Liverpool in the 2010-11 season. After a 2-2 draw at Anfield, the match went to penalties, with Northampton emerging victorious, adding one of the most remarkable chapters to their history.
3. Sheffield Wednesday vs Manchester United (1991)
In the 1991 League Cup final, Sheffield Wednesday led by former United boss Ron Atkinson, managed to upset the heavily fancied Manchester United side managed by Alex Ferguson by a solitary goal scored by John Sheridan. However, the Red Devils would return to Wembley the following season to win the cup for the first time in their history.
4. York City vs Manchester United (1995-96)
In the 1995-96 second round, Manchester United we’re once again at the wrong end of a humiliating 3-0 defeat to York City at Old Trafford. Even though United managed to win the second leg 3-1, York City progressed on aggregate, marking one of the most surprising upsets in the competition’s history.
5. Birmingham City’s Victory (2010-11)
Birmingham City’s victory in the 2010-11 final against Arsenal is another standout shock. The Blues of St Andrews were huge underdogs before kick off but they managed to clinch a 2-1 victory in the dying seconds to secure their first major trophy in 48 years.

6. Swindon Town’s Triumph (1968-69)
Swindon Town, then a Third Division side, made history by winning the League Cup in 1969. They managed to beat Arsenal 3-1 in a match that went to extra time, showcasing the unpredictability and the charm of the competition. Roger Smart and Don Rogers got the goals for The Robins in this incredible victory at Wembley.
7. Boro Becomes The Bride (2003-04)
After finishing runners up twice in the mid 90’s the bridesmaids finally became the bride when Steve McClaren’s Boro lifted the League Cup in 2004. Middlesbrough dumped out Brighton & Hove Albion, Wigan Athletic, Everton, Tottenham Hotspur and Arsenal before beating Bolton Wanderers in the final at Millennium Stadium.
8. MK Dons Humbling Manchester United (2014-15)
In 2014, four time winners at the time Manchester United we’re victims of another shock result as League one side MK Dons, humbled the Reds in a 4-0 win in the second round of the 2014-15 competition. Will Grigg was on fire and scored a brace to put The Dons ahead before Benik Afobe bagged himself a brace also to send the League one outfit into round three.
9. Aston Villa vs Manchester United (1993-94)
The 1993-94 final witnessed Aston Villa upsetting Manchester United, a team that was on its way to a domestic double. Villa triumphed with a 3-1 victory, proving that even the most formidable teams could be beaten on the day. Former United boss, Big Ron once again being a thorn in Alex Ferguson’s side.
10. The boys from Birkenhead (1999-00)
In the last League Cup final at the old Wembley, we saw a first appearance for First Division Tranmere Rovers who took on the mighty Foxes who had reached the final on three of the last four occasions. John Aldridge’s Rovers, we’re narrowly beaten in the final 2-1 but credit goes to the boys from Birkenhead who surprisingly made it all the way to Wembley.
In Summary
The League Cup has been a breeding ground for shock results and remarkable upsets, with smaller clubs often rising to the occasion to defeat more established sides. These moments not only add to the allure and charm of the competition but also cement its place as one of the most unpredictable and exciting domestic football competitions in England. The unpredictable nature of the League Cup ensures that it remains a captivating spectacle for football fans around the world.



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