Fleetwood Town produced one of the biggest shocks in EFL Cup history on Tuesday night, eliminating Premier League champions Arsenal after a dramatic penalty shootout at Highbury Stadium.

The League Two side held Mikel Arteta's team to a 1-1 draw before winning 5-3 on penalties, with goalkeeper Jay Lynch saving Bruno Guimaraes's spot kick before Conor Haughey converted the decisive effort.

Ranked 84 places below Arsenal in the English football pyramid, Fleetwood defied the odds to reach the quarter-finals for the first time in their history.

Fleetwood's triumph was only the second time that the top-flight champions have been knocked out of the competition by a fourth-tier side after Chester City beat Leeds United 3-0 in 1974 .

The EFL Cup has seen plenty of major upsets over the years and Sports Mole has taken a look at five of the biggest giant-killings in the competition's history.

Swindon Town 3-1 Arsenal (1969)

Swindon Town's finest hour. 1969 League Cup Final. Arsenal v Swindon Town at Wembley. Don Rogers runs amok as a third division side lifts the cup. Stupid rules denied them a place in next season's Fairs Cup. #stfc #swindontown #swindontownfc #football https://t.co/dajboC8rpP

— TJS Sports (@SportsTjs) August 7, 2022

Swindon Town produced a stunning upset in the 1969 final, defeating an Arsenal side who were two divisions above them.

The Third Division club took the lead through Roger Smart, but Bobby Gould's late equaliser looked to have rescued the Gunners.

However, Don Rogers struck twice in extra time to seal a 3-1 victory and deliver Swindon the trophy in a historic triumph for the Robins.

Queens Park Rangers 3-2 West Bromwich Albion (1967)

The first ever single-legged League Cup final was held in 1967, when third division @QPR beat @WBA 3-2 at Wembley. Come for the scenes of jubilation and homemade banners, stay for that exquisite lettering on the back of QPR's jackets. https://t.co/mRxNgM9oRf

— MUNDIAL (@MundialMag) January 5, 2021

Queens Park Rangers completed a remarkable comeback to beat West Bromwich Albion in the first League Cup final staged at Wembley in 1967.

QPR were a Third Division side, while West Brom were the reigning champions after beating West Ham to win the competition in 1966.

West Brom established a 2-0 half-time lead thanks to a Clive Clark brace and looked set to lift the trophy once more.

However, QPR produced a dramatic turnaround to win 3-2, with goals from Roger Morgan, Rodney Marsh and Mark Lazarus.

It was the first time a Third Division side had won the League Cup and it remains one of the biggest upsets in English football history.

MK Dons 4-0 Manchester United (2014)

Manchester United endured a humiliating evening in August 2014 when League One MK Dons swept them aside 4-0 in the second round.

United, managed by Louis van Gaal, were punished for defensive mistakes by a fearless home side as Will Grigg and Benik Afobe both scored twice.

The Red Devils did not have a shot on target until the 72nd minute and Van Gaal admitted after the game that he was "not shocked" by the defeat.

Bradford City 1-1 Arsenal (3-2 on penalties, 2012)

13 years ago today, Captain Thomas Vermaelen missed a crucial penalty, as Arsenal were shockingly knocked out of the League Cup in the quarter final stage by League Two side Bradford City. This put more pressure on Arsène Wenger & Arsenal, as they were approaching 8 years without a trophy. Bradford beat Aston Villa in the semi final but were thrashed 5-0 by Swansea in the final.

— ‎ابو (@MAA_Gunner) December 11, 2025

Bradford City enjoyed a memorable EFL Cup run in the 2012-13 season, becoming the first fourth tier side to reach the final since Rochdale in 1962.

In their run to the final, the Bantams beat several Premier League sides but it is their quarter-final victory over Arsenal that was the biggest upset.

The League Two side took the lead through Garry Thompson before Thomas Vermaelen scored a late equaliser in the 88th minute to force the tie to penalties.

Bradford ultimately held their nerve in the shootout, winning 3-2 after Santi Cazorla and Vermaelen missed, and they went on to beat Aston Villa in the semi-final before losing to Swansea City at Wembley.

Grimsby Town 2-2 Manchester United (12-11 on penalties, 2025)

Grimsby Town produced a major shock when they knocked Manchester United out of the competition on penalties in August 2025.

The League Two side took a 2-0 lead inside the opening half-hour, with Charles Vernam and Tyrell Warren exposing United's defensive fragility.

However, goals from Bryan Mbeumo and Harry Maguire in the final 15 minutes rescued a draw and took the game to penalties.

An extraordinary shootout followed, with Grimsby's Clark Oduor and United's Matheus Cunha missing as every player on the pitch took a spot kick.

Darragh Burns then scored on his second attempt, before Mbeumo struck the bar to spark jubilant celebrations at Blundell Park.