We will make history when we face Brighton & Hove Albion in the Carabao Cup fourth round at Emirates Stadium, as we bring up our 250th match in the competition's history.

Our first fixture was in September 1966, when Tommy Baldwin scored in a 1-1 draw with Gillingham, and since then we have won the trophy twice, in 1987 and 1993.

As we gear up for our 250th match, let's look back at some of the moments that have made this tournament special for us down the years:

our history

Having not entered the competition for the first six years, we made our debut in 1966/67, beating Gillingham following two replays before bowing out to West Ham United in the third round. 

We would go all the way to the final a year later, losing to Leeds United at Wembley. We suffered final heartbreak again one year on, losing 3-1 to Swindon Town.

We lifted the trophy for the first time in 1987 thanks to two goals from Charlie Nicholas in a 2-1 win over Liverpool. We hoisted the trophy aloft once again in 1993 with the same scoreline, this time coming against Sheffield Wednesday as goals from Paul Merson and Steve Morrow turned the game around for us at Wembley.

It's seems only fitting that 2-1 is our most popular scoreline across the 249 matches so far, with 31 games won by that margin.

Our landmark match against the Seagulls in N5 means we will become just the third team to reach 250 matches in the tournament's history, behind Liverpool and Aston Villa. So far, we have won 140 matches, scoring 461 goals.

Liverpool are our most frequent opponent, going head-to-head on 18 occasions, with our last contest a penalty shootout victory at Anfield in October 2020.

That was one of eight penalty shootouts we've faced in League Cup history, winning on five occasions against Liverpool five years ago, West Bromwich Albion (2013), Doncaster Rovers (2005), Rotherham United (2003) and Millwall (1992).

the wright stuff

In the last round, Eberechi Eze scored his first goal for us in a 2-0 victory over Port Vale, with Leandro Trossard also netting his maiden League Cup goal in Arsenal colours at Vale Park.

The pair joined a long list of players to score for us in the League Cup, with Ian Wright sitting comfortably at the top as our all-time leading scorer in the competition. Wrighty has 29 goals in just 29 appearances, including a goal on his debut in a victory over Leicester City in the 1991/92 season.

The most recent players to break into the top 10 goalscorers are Theo Walcott, who netted his first Gunners goal in this competition in the final against Chelsea in 2007, and Eddie Nketiah, who also opened his account for us in the League Cup with two goals in a 2-1 victory over Norwich City in 2017.

Meanwhile, David O'Leary has appeared the most times for us in the tournament, turning out on 70 occasions. He's followed closely by Tony Adams (59), Paul Davis (51), Nigel Winterburn (49) and Kenny Sansom (48) in our top five appearance makers.

Young Guns and comebacks

The competition has seen a flurry of bright young talents showcase their skills over the years. A total of 115 players have made their debuts for us in this competition, including 11 under Mikel Arteta since he took charge of his first League Cup match in 2020 against Leicester.

Club history has also been made in this competition. In September 2024, Jack Porter became our youngest-ever starter when he lined up in goal against Bolton Wanderers at the age of 16 years and 72 days old. Cesc Fabregas (16 years 177 days) against Rotherham, and Jack Wilshere (16 years 266 days) against Sheffield United, are second and third on the list.

To add to that, Fabregas is our current youngest-ever goalscorer, netting in the League Cup against Wolves in December 2003 at the age of 16 years and 212 days. Wilshere added to his history-making start against Sheffield United with a goal, making him the second youngest scorer in our history.

During our League Cup history, we've enjoyed a fair share of dramatic moments. One of which came in our 50th game in the competition, the semi-final second leg of the 1986/87 edition against rivals Tottenham. 

Having lost the first leg 1-0 at Highbury, our situation worsened when we went 1-0 down in the second leg. With the aggregate score at 2-0, the PA announcer at White Hart Lane prematurely announced ticket sales for the final at Wembley. That gave our players all the motivation they needed to mount a fight back as second-half goals from Viv Anderson and Niall Quinn forced a semi-final replay, which we won 2-1 to advance to the final, where we lifted our first League Cup and heralded in an era of trophy success.

Over 25 years later and we produced a comeback that would go down in the history books as we travelled to Reading in the fourth round of the tournament. Disaster struck as we conceded four times inside the first 37 minutes at the Madejski Stadium. But goals from Olivier Giroud, Laurent Koscielny and a double from Theo Walcott helped us come from 4-0 down to draw 4-4 and send the game to extra time. 

Walcott completed his hat-trick in extra-time as two goals from Marouane Chamakh rounded off a remarkable 7-5 win in Berkshire to become the first team in the tournament to come from four goals down to win. The contest is also the joint-highest scoring match in League Cup history, along with Dagenham & Redbridge 6-6 Brentford in 2014.

Stats provided by Opta - correct as of 27/10/25