Man City 1-2 Arsenal: 27 Oct, 2004
Goals for two of Arsenal's competititve debutants. Robbie Fowler's last-minute effort looked to have sent this one into extra-time, but there'd be more drama to come...
Robin van Persie: Like Thierry Henry before him, Van Persie would be converted by Wenger from winger to prolific striker. After making his first substitute appearance in the Community Shield against Manchester United, the Dutchman earned his first start in this game, and he netted the opener. Scored 132 goals in 277 games, including 30 league goals in his final season, before joining Sir Alex Ferguson's Old Trafford revolution in summer 2012. After helping Fergie's men win the title in his first year, things went somewhat downhill and he joined Fenerbahce for just under £4m this summer.
Daniel Karbassiyoon: Few outside Arsenal circles will remember Arsenal's American-born utility man, who made this a debut to remember by netting the late winner off the bench as an 82nd-minute sub. After joining as a striker, Karbassiyoon was converted to left-back and played three times under Wenger. He joined Ipswich on loan later in the season before making a permanent switch to Burnley the following summer, but a string of injuries forced him into retirement at just 22. Now a North American scout for the Gunners, Karbassiyoon is widely credited for unearthing Joel Campbell and Gedion Zelalem.
Seb Larsson: Another of the nearly-made-it brigade, Larsson featured as a left-back in this game despite making his name in the reserves as a central midfielder. Three successful appearances in the season's competition earned him the same number in the league the following campaign, before a hugely successful loan spell at Birmingham was made permanent by the West Midlands club in 2006. A Sweden international since 2008, he joined Sunderland on a free in 2011. Scored against Arsenal at the Emirates in his debut campaign, prompting Wenger to suggest he was the best free-kick taker in the top flight.
Philippe Senderos: Signed at 17 from Swiss outfit Servette, the promising centre-back had to wait almost two years for his first-team bow in this game. Starting alongside Pascal Cygan at the heart of defence, Senderos would go on to become a key member of Arsenal's successful sides of the mid-noughties and make 84 league appearances. Played in the 2005 FA Cup final. After falling out of favour he was shipped out on loan to AC Milan and Everton before signing for Fulham on a free in June 2010. After a brief stint at Valencia in 2014 (er, remember that?), he landed back in England with Aston Villa.
Arturo Lupoli: A first start at the City of Manchester wasn't quite the catalyst for a glittering career in north London. He bagged twice against Everton in his next League Cup game, and also featured against Manchester United and Sheffield United that season. But, after a promising run the following campaign - he even made his league debut against Blackburn - the young Italian's progress stunted. He joined Derby on loan in 2006/07 before signing permanently for Fiorentina, but a string of average loan spells proved disappointing. Eventually he fell down the Italian leagues with Ascoli, Grosetto and Varese before hot-footing to Hungary with Budapest Honved. There was something of a redemption story, though: in February 2015 he joined Frosinone, who won promotion to Serie A for the first time.