The Carabao Cup Round of 16 matches were marked by surprise upsets and dramatic penalty shootout battles.

The 2026/27 Carabao Cup Round of 16 delivered dramatic penalty shootouts that secured Liverpool, Manchester City, and fourth-tier club Fleetwood Town places in the quarter-finals. All three sides battled through tightly contested fixtures to confirm their progression, with Fleetwood stealing the spotlight after eliminating Arsenal.

Liverpool beat Chelsea 6-5 on penalties after both sides drew 1-1 across normal time at Anfield. Manchester City also required a penalty shootout to knock out Brighton & Hove Albion, while Fleetwood Town pulled off a major shock by eliminating Arsenal.

These three matches highlighted exactly how the English League Cup produces wildly unpredictable outcomes. Pre-match superiority on paper never guarantees victory, especially when a tie is ultimately decided from the penalty spot.

Liverpool Eliminate Chelsea After Penalty Shootout

Liverpool secured their quarter-final berth after overcoming Chelsea in a hard-fought clash. After 90 minutes ended deadlocked at 1-1, The Reds claimed a 6-5 win in the resulting penalty shootout.

Chelsea took an early lead through Morgan Rogers at the Anfield Stadium fixture, which kicked off early Thursday morning WIB. The penalty was awarded after Ryan Gravenberch fouled Moises Caicedo inside the box, with Rogers' strike beating Liverpool Goalkeeper Giorgi Mamardashvili.

Liverpool responded quickly. In the 43rd minute, the hosts were awarded their own penalty when Wesley Fofana committed handball while attempting to clear a corner kick.

Cody Gakpo converted cleanly, placing his shot into the bottom corner beyond the reach of Chelsea keeper Mike Penders. The 1-1 scoreline held going into the half time break.

Liverpool increased pressure in the second half searching for a winning goal. Ronald Araujo went close with a headed effort, only for Penders to pull off a sharp save.

Chelsea also threatened repeatedly on counter attacks. Morgan Rogers saw a strike blocked by Joe Gomez, before Penders denied another effort from Bradley Barcola. At the opposite end, Mamardashvili stopped Marco Palestra's attempt, while Florian Wirtz's shot was blocked by Levi Colwill.

No additional goals were scored before normal time expired. The tie proceeded to penalties, with Liverpool eventually taking the 6-5 win after Wesley Fofana blazed his effort over the crossbar. That miss ultimately confirmed Chelsea's exit from the competition.

Manchester City Edge Brighton Via Penalty Shootout

Manchester City were also forced to go to penalties to lock in their quarter-final ticket. Playing at the Etihad Stadium, The Citizens drew 2-2 with Brighton before claiming a 4-3 shootout victory.

Brighton mounted a stubborn challenge, taking the lead on two separate occasions. Malick Yalcouye opened the scoring in the 30th minute, finishing a delivery from Georginio Rutter.

Manchester City equalised with a long range strike from Mateo Kovacic hit from outside the penalty area, leaving the score 1-1 at the end of the first half.

After the restart, Brighton retook the lead. Rutter converted Jaouen Hadjam's assist to put the visiting side 2-1 up.

Manchester City refused to fold, levelling the score once again in the 72nd minute. Rayan Cherki's low free kick deflected off Vitor Reis and crossed the Brighton goal line, with the own goal tying the match at 2-2.

This score held until full time, sending the fixture to penalties.

Manchester City won the shootout after converting four out of five attempts. Brighton only successfully scored three of their penalties, falling to a 3-4 defeat.

Fleetwood Town Knock Out Arsenal, The Biggest Upset Of The Fourth Round

The most shocking drama of the round came from Fleetwood Town. This League Two, fourth tier English Football club eliminated Arsenal following a 1-1 normal time draw, before winning 5-3 on penalties at Fleetwood's Highbury Stadium.

Fleetwood did not merely sit back and defend against opponents ranked far above them in the football pyramid. The hosts competed aggressively from the first half, taking the lead in the 21st minute through Aaron Loupalo-Bi.

Arsenal attempted to rally after going behind. The Gunners increased their attacking intensity in the second half, eventually equalising through Viktor Gyokeres.

Arsenal's situation worsened late in the fixture. 16-year old winger Max Dowman received a straight red card in the 85th minute for unsporting conduct, forcing Arsenal to play out the remainder of the match with 10 men.

Despite their numerical advantage, Fleetwood could not score a late winning goal. The 1-1 deadlock forced the tie to be decided via penalties.

Fleetwood delivered a flawless performance from the spot. Ronan Coughlan, Harrison Neal, Will Davies, Andy Cannon, and Conor Haughey all successfully converted their penalties.

Arsenal kept their hopes alive with successful strikes from Martin Odegaard, Kai Havertz, and Viktor Gyokeres. However Bruno Guimaraes' missed penalty proved the decisive turning point, clearing the way for Fleetwood's 5-3 victory.