Arsenal's last defence of the League Cup came in late September 1993. The Gunners were drawn away to Huddersfield Town in the Second Round, with the first round played away at Leeds Road. Goals for Kevin Campbell, Paul Merson and a hat-trick for Ian Wright gave Arsenal a thumping 5-0 victory. In the second leg at Highbury two weeks later, an Alan Smith goal gave Arsenal a 1-1 draw (6-1 victory on aggregate) in front of a crowd of just 18,789. Next up in the third round came the visit of Norwich City to Highbury. The Canaries had surprised everyone the previous season after finishing third in the inaugural Premiership season and were in the middle of a UEFA Cup tie with Bayern Munich, having beaten the Bavarian side 2-1 at the Olympic Stadium.

Norwich visited Highbury at the end of November 1993. an Ian Wright goal cancelled out a Norwich lead from a goal by Ian Crook with the match ending in a 1-1 draw. The two sides met again in the League four days later and for those who often extol the reign of George Graham (particularly when putting down our incumbent boss) there’s a tendency to whitewash certain facts about GG’s reign. Norwich’s visit to Highbury in the League at the end of October came on the back of three straight 0-0 draws away at Liverpool, at home to Manchester City and away at Oldham Athletic. GG’s boys made it four scoreless draws on the bounce against Norwich.

Mercifully though, the League Cup replay at Carrow Road finally saw Arsenal burst into life with a 3-0 victory secured by goals from Paul Merson and two for Ian Wright. This victory stretched Arsenal’s unbeaten run in Cup competitions to an incredible twenty three games since losing in the third round of the FA Cup to Wrexham in January 1992, going into a last sixteen tie with Aston Villa, who had been runners up during the inaugural Premiership season. At the end of November, the run however ended in front of a crowd of 26,453, as a goal for Dalian Atkinson inflicted a 0-1 defeat on Arsenal. In 1994/95, Arsenal were drawn against Hartlepool United. The first leg had been away at Victoria Park with a crowd of 4,421.

Goals for Tony Adams, Paul Merson, Alan Smith and two for Ian Wright earned Arsenal a 5-0 victory. Two weeks later back at Highbury, a crowd of 20,520 turned out for the Second leg. Goals for Kevin Campbell and Paul Dickov. At the end of October 1994, Arsenal would be drawn away to Oldham Athletic nearly five years on to the day when the Latics dumped Arsenal out of the Cup (however Boundary Park would now be without the plastic pitch). The surprisingly low crowd of 9,303 witnessed a goalless draw. The replay occurred at Highbury two weeks later. The crowd of 22,746 saw a 2-0 win for Arsenal with two goals from Paul Dickov.

At the end of November 1994, Arsenal met Sheffield Wednesday in the fourth round around eighteen months on from their League Cup and FA Cup Final battles in 1993. In front of a crowd of 27,390, two of their Cup final tormentors struck again, as goals from Steve Morrow and Ian Wright earned Arsenal a 2-0 victory to progress to the Quarter Finals. In the last eight, Arsenal faced Liverpool away at Anfield. A goal for Ian Rush on the hour inflicted a 0-1 defeat on Arsenal. Liverpool went on to win the League Cup that season. That defeat however was George Graham's final game in charge of Arsenal, as he had been sacked one month later. The first League Cup tie for Arsenal under the management of Bruce Rioch came in September 1995, against ironically, the same side the Gunners played in the Second Round the previous season – Hartlepool United.

The first leg this time had been played away. Goals for Ian Wright and two for Tony Adams earned Arsenal a 3-0 victory. The second leg came in early October at Highbury. Two goals for Dennis Bergkamp and a hat-trick for Dennis Bergkamp gave Arsenal a 5-0 victory and an 8-0 win on aggregate. Three weeks later, Arsenal would be drawn away against Barnsley. Goals for Dennis Bergkamp, Martin Keown and Steve Bould earned Arsenal a 3-0 victory. At the end of November, Sheffield Wednesday came to Highbury for the fourth round tie. An Ian Wright penalty and a goal for John Hartson earned Arsenal a 2-1 victory. Mark Degryse meanwhile pulled one back for Sheffield Wednesday. The victory set up a Quarter Final tie with Kevin Keegan's Newcastle United side who were riding high at the top of the Premiership table with a six point lead over Man United and a game in hand.

That same day, the incumbent England boss Terry Venables announced he was to resign after Euro '96 because of court cases coming up later in year which he felt could interfere with England's efforts to qualify for 1998 World Cup finals. The game would be covered live on ITV. Two goals for Ian Wright earned Arsenal a 2-0 victory and a passage to the Semi Finals and a two legged tie with Aston Villa. The first leg occurred at Highbury on Valentine's Day. Making his final appearance for Arsenal that night would be John Jensen. Arsenal took a two goal lead with two first half goals for Dennis Bergkamp. Two goals for Dwight Yorke however pulled it back to 2-2 by full time. In the second leg a week later, with no further scoring even after extra time, a goalless draw meant that Bruce Rioch's Arsenal crashed out at the Semi Final on the away goals rule.

Bruce Rioch faced the axe the following August and came to be replaced by Arsene Wenger that autumn. Wenger's first League Cup tie would be a trip to the Victoria Ground to play Stoke City in late October. For the first time, as a European qualifier, Arsenal would receive a bye to the third round. Mike Sheron gave Stoke a first half lead, however an Ian Wright equaliser twelve minutes from time earned the Gunners a replay. The replay occurred at Highbury three weeks later. Goals for David Platt, Dennis Bergkamp, Paul Merson and two for Ian Wright earned Arsenal a 5-2 victory, while Mike Sheron would be twice on target for Stoke. Two weeks later however, in the fourth round Arsenal crashed out to Liverpool with a 2-4 defeat at Anfield, with goals for Steve McManaman, Patrick Berger and two for Robbie Fowler, while Ian Wright would convert two penalties for Arsenal.

In 1997/98, Arsenal were drawn at home to Birmingham City in the third round. Birmingham City took the lead with a goal from Tony Hey on twenty minutes. Arsenal equalised with a goal from Luis Boa Morte on the hour. The game went into extra time where a penalty from David Platt, another goal from Boa Morte, as well as Alberto Mendez earned Arsenal a 4-1 victory. The fifth round would bring an all Premiership tie with Coventry City at Highbury. This too went to extra time, however a goal from Dennis Bergkamp nine minutes into injury time settled the game with a 1-0 victory. Six days into the new year saw Arsenal face West Ham at the Boleyn Ground in the Quarter Final. Goals for Ian Wright and Marc Overmars gave the Gunners a 2-1 victory, while Samassi Abou would be on target for the Hammers.

That victory would set up a two legged Semi Final with Chelsea, with the first leg at Highbury at the end of January. Goals for Marc Overmars and Stephen Hughes gave Arsenal a 2-1 victory, with Mark Hughes on target for Chelsea. In the interim between the first and second legs of the tie, Chelsea had sacked manager Ruud Gullit, despite him winning their first piece of silverware for twenty six years just over six months prior. He would be replaced by Gianluca Vialli as Player boss. In the second leg at Stamford Bridge, goals for Mark Hughes, Roberto Di Matteo and Dan Petrescu inflicted a 1-3 defeat on the Gunners, while Dennis Bergkamp on target for Arsenal. This meant that the Gunners would lose 3-4 on aggregate. Chelsea went on to win the League Cup, as well as the European Cup Winners Cup. That defeat however would effectively prevent an Arsenal treble as Wenger's side clinched the Premiership and FA Cup Double.

In 1998/99, the competition would receive a new sponsor and now by known as the Worthington Cup. Arsenal would be drawn against Derby County in the third round at Pride Park. A Lee Carsley own goal and Nelson Vivas would give Arsenal a 2-1 win, while Dean Sturridge would be on target for Derby. That victory set up what looked like a mouthwatering tie with Chelsea at Highbury in the fourth round in mid-November. However, that year the Champions League had expanded the number of entrants and group matches and as a result, Arsene Wenger deemed it appropriate to opted to field a mostly second string side with the exception of Dennis Bergkamp. Chelsea however were mostly fielding their strongest side. As a result, the Blues inflicted a 0-5 hammering on Arsenal.

The outrage from some fans at having paid full price to witness such a weakened side take a hammering to a first choice Chelsea side meant that Arsenal were from here on in willing to lower the cost of admission for League Cup fixtures in light of the second string selections. In 1999/2000, Arsenal's last League Cup campaign of the millennium was a home draw to Preston North End. A crowd of just 15,239 turned out at Highbury for the tie. Goals for Nwankwo Kanu and Stefan Malz earned Arsenal a 2-1 win (the game was neither bad, nor a thriller, but Preston actually had a player at centre half called Michael Jackson!). This set up a fourth round tie with Middlesbrough at the end of November.

Goals for Thierry Henry and Davor Suker were cancelled out by two for Boro's Hamilton Rikard. The game therefore ended 2-2 at the end of extra time and went to a penalty shoot out, where Boro eliminated the Gunners 3-1 on penalties (the Gunners would go on to be eliminated from the FA Cup and the UEFA Cup Final from a shoot-out defeat also that season). Arsenal's first League Cup tie of the new millennium came on the first day of November 2000, against a newly promoted Ipswich Town side who were having a good run in the Premiership at the time. The tie came on the same day that Double squad legend George Armstrong tragically collapsed from a brain haemorrhage at the Arsenal training ground.

The 'Tractor Boys' had took the lead with a goal from Jamie Clapham in just two minutes. Ahead of half time, Arsenal equalised with a goal from Igor Stepanovs on his debut. In the final minute however, Ipswich Town had stole the tie with a last minute goal from Jamie Scrowcroft with a 1-2 defeat. In 2001/02, Arsenal's entry into the League Cup came as late on as Guy Fawkes Night in early November. Arsenal were drawn at home to Man United for a game originally scheduled for 10th October, however this game had to be moved due to Man United having a rearranged Champions League fixture that night, that was originally to be played on 12th September 2001, but were forced to cancel due to the horrific events in New York the day before.

This tie was then scheduled to be played on 7th November, but again needed to be moved forward twenty four hours due to an England fixture with Sweden which was arranged the following Saturday. To complicate matters further, both teams played a match just one day prior to this tie. Arsenal had suffered a rare humiliation that season, by losing 2-4 to Charlton Athletic on live television. Man United meanwhile lost 1-3 away to Liverpool, also shown live on Sky Sports. Rather than a tie between Arsenal and Man United, this fixture came to be something of a nuisance and unfathomably for what was supposed to be a marquee fixture between England's two best teams during the early noughties.

Such was the lack of demand for this fixture than a actually managed to get a ticket for free from someone I knew who couldn't shift the ticket for a game they no longer wished to attend (arguably, this was the League Cup's lowest ebb for a trophy which has often had a long history as a much maligned competition). The fixture failed to sell out Highbury, with a crowd of 30,693. Arsenal that night fielded a mostly second string side which included the like of Oleg Luzhny, Igor Stepanovs and Jermaine Pennant, with the like of Rohan Ricketts, John Halls and Carlin Itonga on the bench. Man United meanwhile had mostly a youth side with Luke Chadwick, Ronnie Wallwork and the late Jimmy Davis who tragically died in a road traffic accident less than two years later.

By half time, Arsenal were three goals up with a hat-trick from Sylvain Wiltord. Into the second half, Arsenal stretched their lead further with a penalty from Nwankwo Kanu. With twenty minutes to go, debutant John Halls found himself sent off for two bookable offences within a minute of each other. Arsenal however held on for a 4-0 win – their biggest over Man United for thirty years and it only took ten men (despite this fact, tie is most probably one largely forgotten even by even the most ardent of Arsenal or Man United fans). This set up a fourth round tie for the Gunners at home to Grimsby Town at the end of the month. The crowd of just 16,917 who bothered to turn out saw goals for Edu and Sylvain Wiltord secure a 2-0 victory.

By mid-December, Arsenal faced a Quarter Final tie away to Blackburn Rovers. In front of a crowd of 13,278, goals for former Barcelona and Man United legend Mark Hughes and a hat-trick for Matt Jensen meant a 0-4 thumping for a mostly second string Arsenal side which included Japanese World Cup star Junichi Inamoto and Greek under-21 international Stathis Tavlaridis. Blackburn went on to win the League Cup that season by beating Spurs in the final at Cardiff. One odd fact about that final however is that, shown as it was on live on ITV, its viewing figures exceeded that of that year's FA Cup Final between Arsenal and Chelsea (despite the fact that Blackburn's semi final tie with Sheffield Wednesday on ITV Digital registered less than a thousand viewers!)

Arsenal's League Cup run in 2002/03 started in early November with a third round tie with Sunderland at Highbury. Just 19,059 turned out at Highbury for the tie to watch a mostly second string side, however included a Robert Pires recovering from a knee injury suffered against Newcastle United in the FA Cup in March, which kept him out of Arsenal's 2001/02 run as well as the 2002 World Cup. Pires opened the scoring on twelve minutes, followed by a second from Francis Jeffers just past the half hour. In the second half however, goals for Kevin Kyle, Marcus Stewart and Darren Williams meant a 2-3 defeat for the Gunners.

In 2003/04, the competition was had changed sponsor again and this time be known as the Carling Cup. The Cup was also thrown something of a life line due to the axing of the Champions League Second Round group phase, replacing a six game round robin phase with the simple home and a away leg. This allowed Champions League competitors a less crowded fixture list to put more effort into the League Cup competition. This was noticeable in the fact that Arsenal's League Cup runs started to run a bit longer. Arguably, Arsenal also acquired a better calibre of youth player to field in the competition. Arsenal were drawn at home to Rotherham United at the end of October, in a game which gave a debut to a sixteen year old Cesc Fabregas who became Arsenal's youngest debutant, as well as an eighteen year old Gael Clichy.